Objectives

To synthesize acetylsalicylic acid and methyl salicylate

Introduction:
Synthesis of Aspirin
A reactant containing a carboxylic acid group (COOH) and another reactant containing an
alcohol group (OH), they react together in a condensation reaction to form an ester (
COOR). Acetylsalicylic acid (aspirin) will be formed by reacting salicylic acid and acetic
anhydride in the presence of phosphoric acid acid (H+). The acid acts as a catalyst in speeding up
the reaction as it removes water from the products, pushing the equilibrium reaction forward.
Here, the water will react with excess acetic anhydride to convert it to acetic acid. After
crystallization, the crystals will be collected by vacuum filtrating using a Buchner funnel setup to
remove the acetic acid from the final aspirin product.

Figure 1. Reaction of salicylic acid with acetic anhydride. Source:

http://www2.volstate.edu/chem/1110/Synthesis_of_Aspirin.htm

Synthesis of Oil of Wintergreen

Oil of wintergreen will be synthesized by reacting methanol with salicylic acid in a hot water
both using sulphuric acid as a catalyst. Methyl salicylate in Oil of Wintergreen has a distinct
minty odor. Oil of Wintergreen is used also as ointments for the relief of muscle pain and
cramping as salicylic acid has analgesic properties. Esters, in general, have sweet, fruity smells.

Figure 2. Reaction of salicylic acid with methanol. Source:

http://www.uccs.edu/Documents/chemistry/nsf/WintergreenExperiment.pdf

Materials

Acetic Anhydride
Methanol, ethanol
Salicylic acid
Sulfuric acid, phosphoric acid

Data
Table 1. Synthesis of Aspirin
Data
2.51
0.0182
2.47
0.0137
3.28

Mass of salicylic acid (+/-0.01g)

Moles of salicylic acid (mol)
Mass of aspirin collected (+/-0.01g)
Moles of aspirin collected (mol)
Theoretical yield of aspirin (g)
Percent yield
Observation
Final product slightly smells of acetic acid
Final product is white and flaky

Table 2. Synthesis of the Oil of Wintergreen

Observation

Color
Colorless,clear
Smell
Sweet, minty smells
Other characteristics
Formation of crystals on side of the test tube
Calculations: Theoretical yield of aspirin: Salicylic acid (SA) is the limiting reactant as an
excess of acetic anhydride (5.00mL) was used.
0.0182 mol SA

1 mol aspirin 180.16 g aspirin

=3.28 g
1mol SA
1 mol aspirin

Percent yield of aspirin:

actual yield
2.47 g
100=
100=75.3
theoretical yield
3.28 g
Conclusion
The actual yield of the aspirin was 2.47 grams, resulting in a 75.3% yield, which was around the
value initially expected. Although further tests would need to be performed to determine the
purity of the acetylsalicylic acid (such as a spectroscopic analysis), the objective of synthesizing
aspirin was mostly achieved.
The actual yield of aspirin is lower than the theoretical yield because throughout the synthesis
process (reacting salicylic acid and acetic anhydride) some product may have been lost due to
heating the solution. Also, throughout the purification process (removing acetic acid by a
Buchner funnel setup), not all of the final product may have transferred and some may have been
lost. Furthermore, the purification process may have not resulted in a pure enough product; as
such, much of the aspirin yield mass could be due to water and salicylic acid (if the aspirin was
not pure before crystallization). Also, there is always error due to the reverse reaction of the
synthesis of aspirin.
The reaction was under for only 10 minutes. If the reaction is heated for a longer amount of time
and also cooled for a longer amount of time, this may lead to a more complete reaction and thus
lessen the amount of crude product. Phosphoric acid was used in this experiment, which has a
pKa of 2.12. Using sulphuric acid instead of phosphoric acid may result in a higher yield as the
reaction will be driven more forward as sulphuric acid has a higher pKa and completely
dissociates in solution1. Using a higher concentration of acid or volume may also result in a
higher yield.

1Source: Zumdahl 6th Ed.