Laciste, Jayme Paolo D.

Group 3-U2L Chem 40

Exercise 12: Synthesis of Aspirin

I: Introduction

Aspirin , also known as acetylsalicylic acid is a salicylate drug, often used as an

analgesic to relieve minor aches and pains, as an antipyretic to reduce fever, and as an
anti-inflammatory medication.

Aspirin also has an antiplatelet effect which under normal circumstances binds
platelet molecules together to repair damaged blood vessels. This is why aspirin is used in
long-term, low doses to prevent heart attacks, strokes, and blood clot formation in people
at high risk for developing blood clots. It has also been established that low doses of
aspirin may be given immediately after a heart attack to reduce the risk of another heart
attack or of the death of cardiac tissue. Salicylic acid is the active ingredient in aspirin
that causes pain relief. However this acid is too harsh on the mucous membranes in the
mouth, esophagus, and stomach. An acetyl group is added to buffer the effects of the acid.

Figure I: Balanced Chemical Equation for the synthesis of aspirin

O O O O
H H
O O O O O CH3 HO O
H H2PO4
+ +
CH3 CH3 O CH3

Salicylic acid Acetic Anhydride Acetylsalicylic acid Acetic acid

mp 160oC bp 139oC (aspirin)
M.W. 102, d 1.08 oC
M.W. 138 mp 135 -136
M.W. 180
II: Objectives

1. To be introduced to concept of organic analysis

2. To synthesize acetylsalicylic acid from salicylic acid by nucleophilic acyl
substitution.
3. To differentiate acetylsalicylic acid from salicylic acid by simple chemical
tests.
III: Materials and Methods

A) Schematic Diagram
B). Set-Up

Figure 2: Heating Set-Up and Suction Filtration Set-Up

C). List of Necessary Chemicals and Reagents

Name and Function in the Physical Hazards Precautions

Structure Experiment Properties; MW
(g/mol),
MP/BP(0C),
Density (g/mL),
Apperance
Salicylic acid Reagent 138.10, Pulmonary
160(MP), N.A. Irritants
Powder –like
white solid
matter
Acetic anhydride Reagent 102.00, 139(BP), Corrosive and
1.08, Clear, Flammable
colorless
homogenous
liquid
Water Solvent 18.02, 100(BP), Completely Safe
1, Clear
Homogenous
Liquid

98.00, 158 (BP), Extremely

Phosporic acid Catalyst 1.69, Clear Corrosive
(concentrated) Colorless Thick
Liquid

Diethyl ether Solvent 74.12, 34 (BP), Toxic and

0.71, Clear Flammable
Colorless Liquid

Petroleum Solvent Flammable

Ferric Chloride Differentiating 162.2, 306 (BP), Corrosive

agent 2.90, Blood-like
thick, opaque
liquid.
IV Data

Weight of Watch Glass and Salicylic Acid ……………………. _________ g

Weight of Empty Watch Glass…………………………………. _________ g
Weight of Salicylic Acid……………………………………….. _________ g
Volume of Acetic Anhydride ………………………………….. _________ mL
Volume of 85% Phosporic Acid…………. ….………………. _________ drops
Time of heating ………………………………………………. __________ min
Total amount of water added to product …………………….. ___________mL
Weight of Filter Paper plus Product………………………….. ___________g
Weight of Dry Filter Paper……………………………………. __________g
Weight of Product ……………………………………………. __________ g
Percent Yield…………………………………………………. ___________%
Theoretical Yield ……………………………………………. ___________g
Estimated loss in washing (at 3.3 mg / mL)…………………… __________g
Melting point of product……………………………………… __________oC

V Sample Calculations
VI Results and Discussions

VII: References:

Borer, L.L. and E. Barry (March, 2000). Synthesis and Characterization of Aspirin and &
compostion of Aspirin tablet. Journal of Chemical Education, Volume 77 issue no.3. Retrieved
from
http://docs.google.com/gview?a=v&q=cache:BVWWlhenVEAJ:employeeweb.cgc.maricopa.edu
/k/ri/krishnaswamy/CHM230LLProcedures/Synthesis%2520and%2520Characterization%2520of
%2520Aspirin.pdf+characterization+of+aspirin&hl=tl&gl=ph

Schneider, R.F. (October, 2006). Syntheis of Aspirin.Che 134, (28). Retrieved from
http://www.ic.sunysb.edu/Class/che134/susb/SUSB028.pdf

O’ Neal, J.M., et. Al. (2001) The Merck index : an encyclopedia of chemicals, drugs, and
biologicals; Whitehouse Station NJ, Merck