Ester

4/27/2018 Ester - Wikipedia
Ester
In chemistry , an ester is a chemical compound deriv ed from an acid (organic or
inorganic) in which at least one –OH (hy droxy l) group is replaced by an –O–alky l (alkoxy )
group. [1] Usually , esters are deriv ed from a carboxy lic acid and an alcohol. Gly cerides,
which are fatty acid esters of gly cerol, are important esters in biology , being one of the
main classes of lipids, and making up the bulk of animal fats and v egetable oils. Esters with
low molecular weight are commonly used as fragrances and found in essential oils and
A carboxylate ester.
pheromones. Phosphoesters form the backbone of DNA molecules. Nitrate esters, such as
R and R′ denote any
nitrogly cerin, are known for their explosiv e properties, while poly esters are important alkyl or aryl group. R
plastics, with monomers linked by ester moieties. can also be a
hydrogen atom.
Contents
Nomenclature
Etymology
IUPAC nomenclature
Orthoesters
Inorganic esters
Structure and bonding
Physical properties and characterization
Characterization and analysis
Applications and occurrence
Preparation
Esterification of carboxylic acids
Alcoholysis of acyl chlorides and acid anhydrides
Alkylation of carboxylate salts
Transesterification
Carbonylation
Addition of carboxylic acids to alkenes
Other methods
Reactions
Addition of nucleophiles at carbonyl
Reduction
Claisen condensation and related reactions
Other reactions
Protecting groups
List of ester odorants
See also
References
External links
https://en.wikipedia.org/wiki/Ester#Reactions 1/13
Nomenclature
Etymology
The word 'ester' was coined in 1848 by a German chemist Leopold Gmelin, [2] probably as a contraction of the
German Essigäther, "acetic ether".
IUPAC nomenclature
Ester names are deriv ed from the parent alcohol and the parent acid, where the latter may be organic or inorganic.
Esters deriv ed from the simplest carboxy lic acids are commonly named according to the more traditional, so-called
"triv ial names" e.g. as formate, acetate, propionate, and buty rate, as opposed to the IUPAC nomenclature
methanoate, ethanoate, propanoate and butanoate. Esters deriv ed from more complex carboxy lic acids are, on the
other hand, more frequently named using the sy stematic IUPAC name, based on the name for the acid followed by
the suffix -oate. For example, the ester hexy l octanoate, also known under the triv ial name hexy l capry late, has the
formula CH3 (CH2 )6 CO2 (CH2 )5 CH3 .
The chemical formulas of organic esters usually take the form RCO2 R′,
where R and R′ are the hy drocarbon parts of the carboxy lic acid and the
alcohol, respectiv ely . For example, buty l acetate (sy stematically buty l
ethanoate), deriv ed from butanol and acetic acid (sy stematically ethanoic
acid) would be written CH3 CO2 C4 H9 . Alternativ e presentations are
common including BuOAc and CH3 COOC4 H9 .
Cy clic esters are called lactones, regardless of whether they are deriv ed
from an organic or an inorganic acid. One example of a (organic) lactone is
γ-v alerolactone. Ethyl acetate derived from an alcohol
(blue) and an acyl group (yellow)
derived from a carboxylic acid
Orthoesters
An uncommon class of organic esters are the orthoesters, which hav e the
formula RC(OR′)3 . Triethy lorthoformate (HC(OC2 H5 )3 ) is deriv ed, in terms of its name (but not its sy nthesis) from
orthoformic acid (HC(OH)3 ) and ethanol.
Inorganic esters
Esters can also be deriv ed from an inorganic acid and an alcohol. Thus, the nomenclature
extends to inorganic oxo acids and their corresponding esters: phosphoric acid and
phosphate esters/organophosphates, sulfuric acid and sulfate esters/organosulfates,
nitric acid and nitrate, and boric acid and borates. For example, tripheny l phosphate is
the ester deriv ed from phosphoric acid and phenol. Organic carbonates are deriv ed from A phosphoric acid
carbonic acid; for example, ethy lene carbonate is deriv ed from carbonic acid and ester
ethy lene gly col.
So far an alcohol and inorganic acid are linked v ia oxy gen atoms. The definition of inorganic acid ester that feature
inorganic chemical elements links between alcohols and the inorganic acid – the phosphorus atom linking to three
alkoxy functional groups in organophosphate – can be extended to the same elements in v arious combinations of
cov alent bonds between carbons and the central inorganic atom and carbon–oxy gen bonds to central inorganic
atoms. For example, phosphorus features three carbon–oxy gen–phosphorus bondings and one phosphorus–
oxy gen double bond in organophosphates,
three carbon–oxy gen–phosphorus bondings and no phosphorus–oxy gen double

bonds in phosphite esters or organophosphites,
two carbon–oxy gen–phosphorus bondings, no phosphorus–oxy gen double bonds but

one phosphorus–carbon bond in phosphonites,
one carbon–oxy gen–phosphorus bondings, no phosphorus–oxy gen double bonds but structure of a generic
two phosphorus–carbon bonds in phosphinites. organophosphate
In corollary , boron features borinic esters (n = 2), boronic esters (n = 1), and borates
(n = 0).
As oxy gen is a group 16 chemical element, sulfur atoms can replace some oxy gen atoms
in carbon–oxy gen–central inorganic atom cov alent bonds of an ester. As a result,
thiosulfinates' and thiosulfonates, with a central inorganic sulfur atom, structure of a generic
phosphite ester
demonstrate clearly the assortment of sulfur esters, that also includes sulfates, sulfites,
showing the lone
sulfonates, sulfinates, sulfenates esters.
pairs on the P
Structure and bonding

Esters contain a carbony l center, which giv es rise to 120 ° C–C–O and O–C–O angles.
Unlike amides, esters are structurally flexible functional groups because rotation about
the C–O–C bonds has a low barrier. Their flexibility and low polarity is manifested in their
phy sical properties; they tend to be less rigid (lower melting point) and more v olatile structure of a generic
(lower boiling point) than the corresponding amides. [3] The pKa of the alpha-hy drogens phosphonite – ester
on esters is around 25. [4] of phosphonous acid
Many esters hav e the potential for conformational isomerism, but they tend to adopt
an s-cis (or Z) conformation rather than the s-trans (or E) alternativ e, due to a
combination of hy perconjugation and dipole minimization effects. The preference for
the Z conformation is influenced by the nature of the substituents and solv ent, if
present. [5][6] Lactones with small rings are restricted to the s-trans (i.e. E)
conformation due to their cy clic structure. structure of a generic
phosphinite.
Physical properties and characterization
Esters are more polar than ethers but less polar than alcohols. They participate in hy drogen bonds as hy drogen-
bond acceptors, but cannot act as hy drogen-bond donors, unlike their parent alcohols. This ability to participate in
hy drogen bonding confers some water-solubility . Because of their lack of hy drogen-bond-donating ability , esters do
not self-associate. Consequently , esters are more v olatile than carboxy lic acids of similar molecular weight. [3]
Characterization and analysis

Esters are generally identified by gas chromatography , taking adv antage of their v olatility . IR spectra for esters
feature an intense sharp band in the range 17 30–17 50 cm−1 assigned to ν C=O. This peak changes depending on the
functional groups attached to the carbony l. For example, a benzene ring or double bond in conjugation with the
carbony l will bring the wav enumber down about 30 cm−1 .
Applications and occurrence

Esters are widespread in nature and are widely used in industry . In nature, fats are in general triesters deriv ed from
gly cerol and fatty acids. [7] Esters are responsible for the aroma of many fruits, including apples, durians, pears,
bananas, pineapples, and strawberries. [8] Sev eral billion kilograms of poly esters are produced industrially annually ,
important products being poly ethy lene terephthalate, acry late esters, and cellulose acetate. [9]
Preparation
Esterification is the general name for
a chemical reaction in which two
reactants (ty pically an alcohol and an
acid) form an ester as the reaction
product. Esters are common in
organic chemistry and biological
materials, and often hav e a
characteristic pleasant, fruity odor.
This leads to their extensiv e use in
the fragrance and flav or industry .
Ester bonds are also found in many Representative triglyceride found in a linseed oil, a triester (triglyceride)
poly mers. derived of linoleic acid, alpha-linolenic acid, and oleic acid.
Esterification of carboxylic acids

The classic sy nthesis is the Fischer esterification, which inv olv es treating a carboxy lic acid with an alcohol in the
presence of a dehy drating agent:
RCO2H + R′OH ⇌ RCO2R′ + H2O
The equilibrium constant for such reactions is about 5 for ty pical esters, e.g., ethy l acetate. [10] The reaction is slow
in the absence of a cataly st. Sulfuric acid is a ty pical cataly st for this reaction. Many other acids are also used such as
poly meric sulfonic acids. Since esterification is highly rev ersible, the y ield of the ester can be improv ed using Le
Chatelier's principle:
Using the alcohol in large excess (i.e., as a solvent).
Using a dehydrating agent: sulfuric acid not only catalyzes the reaction but sequesters water (a reaction product). Other
drying agents such as molecular sieves are also effective.
Removal of water by physical means such as distillation as a low-boiling azeotropes with toluene, in conjunction with a
Dean-Stark apparatus.
Reagents are known that driv e the dehy dration of mixtures of alcohols and carboxy lic acids. One example is the
Steglich esterification, which is a method of forming esters under mild conditions. The method is popular in peptide
sy nthesis, where the substrates are sensitiv e to harsh conditions like high heat. DCC (dicy clohexy lcarbodiimide) is
used to activ ate the carboxy lic acid to further reaction. 4-Dimethy laminopy ridine (DMAP) is used as an acy l-
transfer cataly st. [11]
Another method for the dehy dration of mixtures of alcohols and carboxy lic acids is the Mitsunobu reaction:
RCO2H + R′OH + P(C6H5)3 + R2N2 → RCO2R′ + OP(C6H5)3 + R2N2H2
Carboxy lic acids can be esterified using diazomethane:
RCO2H + CH2N2 → RCO2CH3 + N2
Using this diazomethane, mixtures of carboxy lic acids can be conv erted to their methy l esters in near quantitativ e
y ields, e.g., for analy sis by gas chromatography . The method is useful in specialized organic sy nthetic operations but
is considered too hazardous and expensiv e for large-scale applications.
Alcoholysis of acyl chlorides and acid anhydrides

Alcohols react with acy l chlorides and acid anhy drides to giv e esters:
RCOCl + R′OH → RCO2R′ + HCl

(RCO)2O + R′OH → RCO2R′ + RCO2H
The reactions are irrev ersible simplify ing work-up. Since acy l chlorides and acid anhy drides also react with water,
anhy drous conditions are preferred. The analogous acy lations of amines to giv e amides are less sensitiv e because
amines are stronger nucleophiles and react more rapidly than does water. This method is employ ed only for
laboratory -scale procedures, as it is expensiv e.
Alkylation of carboxylate salts

Although not widely employ ed for esterifications, salts of carboxy late anions can be alky lating agent with alky l
halides to giv e esters. In the case that an alky l chloride is used, an iodide salt can cataly ze the reaction (Finkelstein
reaction). The carboxy late salt is often generated in situ. In difficult cases, the silv er carboxy late may be used, since
the silv er ion coordinates to the halide aiding its departure and improv ing the reaction rate. This reaction can suffer
from anion av ailability problems and, therefore, can benefit from the addition of phase transfer cataly sts or highly
polar aprotic solv ents such as DMF.
Transesterification
Transesterification, which inv olv es changing one ester into another one, is widely practiced:
RCO2R′ + CH3OH → RCO2CH3 + R′OH
Like the hy droly sation, transesterification is cataly sed by acids and bases. The reaction is widely used for degrading
trigly cerides, e.g. in the production of fatty acid esters and alcohols. Poly (ethy lene terephthalate) is produced by the
transesterification of dimethy l terephthalate and ethy lene gly col:[9]
(C6H4)(CO2CH3)2 + 2 C2H4(OH)2 → 1⁄n {(C6H4)(CO2)2(C2H4)}n + 2 CH3OH
Carbonylation
Alkenes undergo "hy droesterification" in the presence of metal carbony l cataly sts. Esters of propionic acid are
produced commercially by this method:
C2H4 + ROH + CO → C2H5CO2R
The carbony lation of methanol y ields methy l formate, which is the main commercial source of formic acid. The
reaction is cataly zed by sodium methoxide:
CH3OH + CO → CH3O2CH
Addition of carboxylic acids to alkenes

In the presence of palladium-based cataly sts, ethy lene, acetic acid, and oxy gen react to giv e v iny l acetate:
C2H4 + CH3CO2H + 1⁄2 O2 → C2H3O2CCH3 + H2O
Direct routes to this same ester are not possible because v iny l alcohol is unstable.
Other methods
Favorskii rearrangement of α-haloketones in presence of base
Baeyer–Villiger oxidation of ketones with peroxides
Pinner reaction of nitriles with an alcohol
Nucleophilic abstraction of a metal–acyl complex
Hydrolysis of orthoesters in aqueous acid
Cellulolysis via esterification [12]
Ozonolysis of alkenes using a work up in the presence of hydrochloric acid and various alcohols.[13]
Anodic oxidation of methyl ketones leading to methyl esters.[14]
Reactions
Esters react with nucleophiles at the carbony l carbon. The carbony l is weakly electrophilic but is attacked by strong
nucleophiles (amines, alkoxides, hy dride sources, organolithium compounds, etc.). The C–H bonds adjacent to the
carbony l are weakly acidic but undergo deprotonation with strong bases. This process is the one that usually
initiates condensation reactions. The carbony l oxy gen in esters is weakly basic, less so than the carbony l oxy gen in
amides due to resonance donation of an electron pair from nitrogen in amides, but forms adducts.
Addition of nucleophiles at carbonyl

Esterification is a rev ersible reaction. Esters undergo hy droly sis under acid and basic conditions. Under acidic
conditions, the reaction is the rev erse reaction of the Fischer esterification. Under basic conditions, hy droxide acts
as a nucleophile, while an alkoxide is the leav ing group. This reaction, saponification, is the basis of soap making.
The alkoxide group may also be displaced by stronger nucleophiles such as ammonia or primary or secondary
amines to giv e amides: (ammonoly sis reaction)
RCO2R′ + NH2R″ → RCONHR″ + R′OH
This reaction is not usually rev ersible. Hy drazines and hy droxy lamine can be used in place of amines. Esters can be
conv erted to isocy anates through intermediate hy droxamic acids in the Lossen rearrangement.
Sources of carbon nucleophiles, e.g., Grignard reagents and organolithium compounds, add readily to the carbony l.
Reduction
Compared to ketones and aldehy des, esters are relativ ely resistant to reduction. The introduction of cataly tic
hy drogenation in the early part of the 20th century was a breakthrough; esters of fatty acids are hy drogenated to
fatty alcohols.
RCO2R′ + 2 H2 → RCH2OH + R′OH
A ty pical cataly st is copper chromite. Prior to the dev elopment of cataly tic hy drogenation, esters were reduced on a
large scale using the Bouv eault–Blanc reduction. This method, which is largely obsolete, uses sodium in the presence
of proton sources.
Especially for fine chemical sy ntheses, lithium aluminium hy dride is used to reduce esters to two primary alcohols.
The related reagent sodium borohy dride is slow in this reaction. DIBAH reduces esters to aldehy des. [15]
Direct reduction to giv e the corresponding ether is difficult as the intermediate hemiacetal tends to decompose to
giv e an alcohol and an aldehy de (which is rapidly reduced to giv e a second alcohol). The reaction can be achiev ed
using triethy lsilane with a v ariety of Lewis acids. [16][17]
Claisen condensation and related reactions
As for aldehy des, the hy drogen atoms on the carbon adjacent ("α to") the carboxy l group in esters are sufficiently
acidic to undergo deprotonation, which in turn leads to a v ariety of useful reactions. Deprotonation requires
relativ ely strong bases, such as alkoxides. Deprotonation giv es a nucleophilic enolate, which can further react, e.g.,
the Claisen condensation and its intramolecular equiv alent, the Dieckmann condensation. This conv ersion is
exploited in the malonic ester sy nthesis, wherein the diester of malonic acid reacts with an electrophile (e.g., alky l
halide), and is subsequently decarboxy lated. Another v ariation is the Fráter–Seebach alky lation.
Other reactions
Phenyl esters react to hydroxyarylketones in the Fries rearrangement.
Specific esters are functionalized with an α-hydroxyl group in the Chan rearrangement.
Esters with β-hydrogen atoms can be converted to alkenes in ester pyrolysis.
A direct conversion of esters to nitriles.[18]
Protecting groups
As a class, esters serv e as protecting groups for carboxy lic acids. Protecting a carboxy lic acid is useful in peptide
sy nthesis, to prev ent self-reactions of the bifunctional amino acids. Methy l and ethy l esters are commonly av ailable
for many amino acids; the t-buty l ester tends to be more expensiv e. Howev er, t-buty l esters are particularly useful
because, under strongly acidic conditions, the t-buty l esters undergo elimination to giv e the carboxy lic acid and
isobuty lene, simplify ing work-up.
List of ester odorants

Many esters hav e distinctiv e fruit-like odors, and many occur naturally in the essential oils of plants. This has also
led to their commonplace use in artificial flav orings and fragrances when those odors aim to be mimicked.
Ester name Formula Odor or occurrence
Allyl hexanoate pineapple
Benzyl acetate pear, strawberry, jasmine
Bornyl acetate pine
Butyl acetate apple, honey
Butyl butyrate pineapple
Butyl propanoate pear drops
Ethyl acetate nail polish remover, model paint, model airplane glue
Ethyl benzoate sweet, wintergreen, fruity, medicinal, cherry, grape
Ethyl butyrate banana, pineapple, strawberry
Ethyl hexanoate pineapple, waxy-green banana
Ethyl cinnamate cinnamon
Ethyl formate lemon, rum, strawberry
Ethyl heptanoate apricot, cherry, grape, raspberry
Ethyl isovalerate apple
Ethyl lactate butter, cream
Ethyl nonanoate grape
Ethyl pentanoate apple
Geranyl acetate geranium
Geranyl butyrate cherry
Geranyl pentanoate apple
Isobutyl acetate cherry, raspberry, strawberry
Isobutyl formate raspberry
Isoamyl acetate pear, banana (flavoring in Pear drops)
Isopropyl acetate fruity
Linalyl acetate lavender, sage
Linalyl butyrate peach
Linalyl formate apple, peach
Methyl acetate glue
Methyl anthranilate grape, jasmine
Methyl benzoate fruity, ylang ylang, feijoa
Methyl butyrate (methyl

pineapple, apple, strawberry
butanoate)
Methyl cinnamate strawberry
Methyl pentanoate (methyl

flowery
valerate)
Methyl phenylacetate honey
Methyl salicylate (oil of Modern root beer, wintergreen, Germolene and Ralgex ointments
wintergreen) (UK)
Nonyl caprylate orange
Octyl acetate fruity-orange
Octyl butyrate parsnip
Amyl acetate (pentyl acetate) apple, banana
Pentyl butyrate (amyl butyrate) apricot, pear, pineapple
Pentyl hexanoate (amyl caproate) apple, pineapple
Pentyl pentanoate (amyl valerate) apple
Propyl acetate pear
Propyl hexanoate blackberry, pineapple, cheese, wine
Propyl isobutyrate rum
Terpenyl butyrate cherry
See also
Amide, an ester analog with oxygen replaced by nitrogen
Cyanate ester
Oligoester
Polyolester
Thioester, an ester analog with oxygen replaced by sulfur
Transesterification
References
1. IUPAC, Compendium of Chemical Terminology, 2nd ed. (the "Gold Book") (1997). Online corrected version: (2006–)
"esters (http://goldbook.iupac.org/E02219.html)".
2. Leopold Gmelin, Handbuch der Chemie, vol. 4: Handbuch der organischen Chemie (vol. 1) (Heidelberg, Baden
(Germany): Karl Winter, 1848), page 182 (https://books.google.com/books?id=4ooMAQAAIAAJ&pg=PA182&lpg=PA182
#v=onepage&q&f=false).
Original text:
b. Ester oder sauerstoffsäure Aetherarten.

Ethers du troisième genre.
Viele mineralische und organische Sauerstoffsäuren treten mit einer Alkohol-Art unter Ausscheidung von
Wasser zu neutralen flüchtigen ätherischen Verbindungen zusammen, welche man als gepaarte
Verbindungen von Alkohol und Säuren-Wasser oder, nach der Radicaltheorie, als Salze betrachten kann,
in welchen eine Säure mit einem Aether verbunden ist.
Translation:
b. Ester or oxy-acid ethers.

Ethers of the third type.
Many mineral and organic acids containing oxygen combine with an alcohol upon elimination of water to
[form] neutral, volatile ether compounds, which one can view as coupled compounds of alcohol and acid-
water, or, according to the theory of radicals, as salts in which an acid is bonded with an ether.
3. March, J. Advanced Organic Chemistry 4th Ed. J. Wiley and Sons, 1992: New York. ISBN 0-471-60180-2.
4. Chemistry of Enols and Enolates – Acidity of alpha-hydrogens (http://pharmaxchange.info/press/2011/02/chemistry-of-e
nolates-and-enols-acidity-of-alpha-hydrogens/)
5. Diwakar M. Pawar; Abdelnaser A. Khalil; Denise R. Hooks; Kenneth Collins; Tijuana Elliott; Jefforey Stafford; Lucille
Smith; Eric A. Noe (1998). "E and Z Conformations of Esters, Thiol Esters, and Amides". J. Am. Chem. Soc. 120 (9):
2108–2112. doi:10.1021/ja9723848 (https://doi.org/10.1021%2Fja9723848).
6. Christophe Dugave; Luc Demange (2003). "Cis−Trans Isomerization of Organic Molecules and Biomolecules:
Implications and Applications". Chem. Rev. 103 (7): Chem. Rev. doi:10.1021/cr0104375 (https://doi.org/10.1021%2Fcr01
04375).
7. Isolation of triglyceride from nutmeg: G. D. Beal "Trimyristen" Organic Syntheses, Coll. Vol. 1, p.538 (1941). Link (http://
orgsynth.org/orgsyn/pdfs/CV1P0538.pdf)
8. McGee, Harold. On Food and Cook ing'. 2003, Scribner, New York .
9. Wilhelm Riemenschneider1 and Hermann M. Bolt "Esters, Organic" Ullmann's Encyclopedia of Industrial Chemistry,
2005, Wiley-VCH, Weinheim. doi:10.1002/14356007.a09_565.pub2 (https://doi.org/10.1002%2F14356007.a09_565.pub
2)
10. Williams, Roger J.; Gabriel, Alton; Andrews, Roy C. (1928). "The Relation Between the Hydrolysis Equilibrium Constant
of Esters and the Strengths of the Corresponding Acids". J. Am. Chem. Soc. 50 (5): 1267–1271.
doi:10.1021/ja01392a005 (https://doi.org/10.1021%2Fja01392a005).
11. B. Neises; W. Steglich. "Esterification of Carboxylic Acids with Dicyclohexylcarbodiimide/4-Dimethylaminopyridine: tert-
Butyl ethyl fumarate" (http://www.orgsyn.org/demo.aspx?prep=cv7p0093). Organic Syntheses.; Collective Volume, 7,
p. 93
12. Ignatyev, Igor; Charlie Van Doorslaer; Pascal G.N. Mertens; Koen Binnemans; Dirk. E. de Vos (2011). "Synthesis of
glucose esters from cellulose in ionic liquids" (http://www.degruyter.com/view/j/hfsg.2012.66.issue-4/hf.2011.161/hf.2011.
161.xml). Holzforschung. 66 (4): 417–425. doi:10.1515/hf.2011.161 (https://doi.org/10.1515%2Fhf.2011.161).
13. Neumeister, Joachim; Keul, Helmut; Pratap Saxena, Mahendra; Griesbaum, Karl (1978). "Ozone Cleavage of Olefins
with Formation of Ester Fragments". Angewandte Chemie International Edition in English. 17 (12): 939–940.
doi:10.1002/anie.197809392 (https://doi.org/10.1002%2Fanie.197809392).
14. Makhova, Irina V.; Elinson, Michail N.; Nikishin, Gennady I. (1991). "Electrochemical oxidation of ketones in methanol in
the presence of alkali metal bromides". Tetrahedron. 47 (4–5): 895–905. doi:10.1016/S0040-4020(01)87078-2 (https://do
i.org/10.1016%2FS0040-4020%2801%2987078-2).
15. W. Reusch. "Carboxyl Derivative Reactivity" (http://arquivo.pt/wayback/20160516073829/http://www.cem.msu.edu/~reus
ch/VirtualText/crbacid2.htm#react2). Virtual Textbook of Organic Chemistry. Archived from the original (http://www.cem.
msu.edu/~reusch/VirtualText/crbacid2.htm#react2) on 2016-05-16.
16. Yato, Michihisa; Homma, Koichi; Ishida, Akihiko (June 2001). "Reduction of carboxylic esters to ethers with triethyl
silane in the combined use of titanium tetrachloride and trimethylsilyl trifluoromethanesulfonate". Tetrahedron. 57 (25):
5353–5359. doi:10.1016/S0040-4020(01)00420-3 (https://doi.org/10.1016%2FS0040-4020%2801%2900420-3).
17. Sakai, Norio; Moriya, Toshimitsu; Konakahara, Takeo (July 2007). "An Efficient One-Pot Synthesis of Unsymmetrical
Ethers: A Directly Reductive Deoxygenation of Esters Using an InBr3/Et3SiH Catalytic System". The Journal of
Organic Chemistry. 72 (15): 5920–5922. doi:10.1021/jo070814z (https://doi.org/10.1021%2Fjo070814z). PMID 17602594
(https://www.ncbi.nlm.nih.gov/pubmed/17602594).
18. Wood, J. L.; Khatri, N. A.; Weinreb, S. M. (1979). "A direct conversion of esters to nitriles". Tetrahedron Letters. 20
(51): 4907. doi:10.1016/S0040-4039(01)86746-0 (https://doi.org/10.1016%2FS0040-4039%2801%2986746-0).
External links
An introduction to esters (http://www.chemguide.co.uk/organicprops/esters/background.html)
Molecule of the month: Ethyl acetate and other esters (http://www.chm.bris.ac.uk/motm/ethylacetate/ethylh.htm)
Retrieved from "https://en.wikipedia.org/w/index.php?title=Ester&oldid=831323428"
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4/27/2018 Ester - Wikipedia

three carbon–oxy gen–phosphorus bondings and no phosphorus–oxy gen double

two carbon–oxy gen–phosphorus bondings, no phosphorus–oxy gen double bonds but

Structure and bonding

Physical properties and characterization

Characterization and analysis

Applications and occurrence

Esterification of carboxylic acids

RCO2H + R′OH ⇌ RCO2R′ + H2O

Using the alcohol in large excess (i.e., as a solvent).

RCO2H + R′OH + P(C6H5)3 + R2N2 → RCO2R′ + OP(C6H5)3 + R2N2H2

Carboxy lic acids can be esterified using diazomethane:

RCO2H + CH2N2 → RCO2CH3 + N2

Alcoholysis of acyl chlorides and acid anhydrides

RCOCl + R′OH → RCO2R′ + HCl

Alkylation of carboxylate salts

RCO2R′ + CH3OH → RCO2CH3 + R′OH

(C6H4)(CO2CH3)2 + 2 C2H4(OH)2 → 1⁄n {(C6H4)(CO2)2(C2H4)}n + 2 CH3OH

C2H4 + ROH + CO → C2H5CO2R

Addition of carboxylic acids to alkenes

C2H4 + CH3CO2H + 1⁄2 O2 → C2H3O2CCH3 + H2O

Addition of nucleophiles at carbonyl

RCO2R′ + NH2R″ → RCONHR″ + R′OH

RCO2R′ + 2 H2 → RCH2OH + R′OH

Claisen condensation and related reactions

List of ester odorants

Ester name Formula Odor or occurrence

Allyl hexanoate pineapple

Benzyl acetate pear, strawberry, jasmine

Bornyl acetate pine

Butyl acetate apple, honey

Butyl butyrate pineapple

Butyl propanoate pear drops

Ethyl benzoate sweet, wintergreen, fruity, medicinal, cherry, grape

Ethyl butyrate banana, pineapple, strawberry

Ethyl hexanoate pineapple, waxy-green banana

Ethyl cinnamate cinnamon

Ethyl formate lemon, rum, strawberry

Ethyl heptanoate apricot, cherry, grape, raspberry

Ethyl isovalerate apple

Ethyl lactate butter, cream

Ethyl nonanoate grape

Ethyl pentanoate apple

Geranyl acetate geranium

Geranyl butyrate cherry

Geranyl pentanoate apple

Isobutyl acetate cherry, raspberry, strawberry

Isoamyl acetate pear, banana (flavoring in Pear drops)

Isopropyl acetate fruity

Linalyl acetate lavender, sage

Linalyl butyrate peach

Linalyl formate apple, peach

Methyl acetate glue

Methyl anthranilate grape, jasmine

Methyl benzoate fruity, ylang ylang, feijoa

Methyl butyrate (methyl

Methyl cinnamate strawberry

Methyl pentanoate (methyl

Methyl phenylacetate honey

Nonyl caprylate orange

Octyl acetate fruity-orange

Octyl butyrate parsnip

Amyl acetate (pentyl acetate) apple, banana

Pentyl butyrate (amyl butyrate) apricot, pear, pineapple