Experiment title: Synthesis of Aspirin

Lebanese American Uni

Aim of the experiment: The aim of this experiment is to produce Aspirin (C9H8O4) via an
esterification reaction between the salicylic acid (C7H6O3) and acetic anhydride (C4H6O3) using
H3PO4 (phosphoric acid) as an acid catalyst and to test Aspirin’s purity using FeCl3 purity test.
Experimental: First, a warm-water bath was prepared using a 250 ml beaker and a hotplate.
While it was heating, 3 g of salicylic acid were weighed and placed in a 125 mL Erlenmeyer
flask. Then 6 mL of acetic anhydride was carefully added using a graduated pipette followed by
10 drops of an H3PO4 solution. The contents of the flask were swirled to mix the reactants
thoroughly. The flask was then stoppered with one hole cork fitted with an inverted Pasteur
pipette. The 125 mL Erlenmeyer flask with the mixture of salicylic acid, acetic anhydride, and
H3PO4 was partially submerged in the water bath and heated for 15 minutes. Then, the flask was
removed from the bath, and while the contents were hot, 5 mL of ice water was added to the
flask all at once to hydrolyze the excess acetic anhydride. Then, once the reaction reached
completion, 35 mL of water was added, and the flask was left to cool to room temperature for
several minutes before placing it in an ice bath for 5 mins. The walls of the flask were scratched
using a glass rod. The mixture then underwent vacuum filtration and was poured onto a pre-
weighed filter paper on a Buchner funnel attached to a filtration flask, connected to a vacuum
system. Once the liquid had been drawn out of the mixture, the crystals were washed with small
amount of ethanol The vacuum filtration apparatus was left on for several minutes to aid in the
drying of the solid product which was then inserted into the oven for approximately 15 mins. The
dry sample with the filter paper was then removed from the oven, weighed, and recorded.
Afterward, a ferric chloride test was performed. Two test tubes were used, one contained a small
sample of salicylic acid and the other acetylsalicylic acid each dissolved in 1 mL methanol. A
few drops of 1% aqueous ferric chloride solution were added using a dropper and the change of
color was observed and recorded.
Results:

+ +
Salicylic acid acetic anhydride Acetylsalicylic Acetic acid
Acid
Theoretically, the reaction occurs in a 1:1 ratio:
𝑛 (𝑠𝑎𝑙𝑖𝑐𝑦𝑙𝑖𝑐 𝑎𝑐𝑖𝑑)/1 = 𝑛 (𝑎𝑐𝑒𝑡𝑖𝑐 𝑎𝑛ℎ𝑦𝑑𝑟𝑖𝑑𝑒)/1
𝑛 (𝑠𝑎𝑙𝑖𝑐𝑦𝑙𝑖𝑐 𝑎𝑐𝑖𝑑) = 𝑚 (𝑠𝑎𝑙𝑖𝑐𝑦𝑙𝑖𝑐 𝑎𝑐𝑖𝑑)/𝑀. 𝑤. (𝑠𝑎𝑙𝑖𝑐𝑦𝑙𝑖𝑐 𝑎𝑐𝑖𝑑) =3 /138.121 = 0.0217 𝑚𝑜𝑙es
𝑛 (𝑎𝑐𝑒𝑡𝑖𝑐 𝑎𝑛ℎ𝑦𝑑𝑟𝑖𝑑𝑒) = 𝑚 (𝑎𝑐𝑒𝑡𝑖𝑐 𝑎𝑛ℎ𝑦𝑑𝑟𝑖𝑑𝑒)/𝑀. 𝑤. (𝑎𝑐𝑒𝑡𝑖𝑐 𝑎𝑛ℎ𝑦𝑑𝑟𝑖𝑑𝑒) =
𝐷𝑒𝑛𝑠𝑖𝑡𝑦 *𝑉𝑜𝑙𝑢𝑚𝑒/𝑀. 𝑤. (𝑎𝑐𝑒𝑡𝑖𝑐 𝑎𝑛ℎ𝑦𝑑𝑟𝑖𝑑𝑒) = 6 𝑥 1.05/102.09 = 0.0634 moles
Hence, according to stoichiometry,
 0.0217 0.0634
Rsalicylic acid = =¿ 0.0217 <Racetic anhydride= =¿ 0.0634, hence salicylic acid is the
1 1
limiting reagent.
Therefore,
n salicylic acid n acetic anhydride
=
1 1

n Aspirin (theoretical) n Salycilic Acid 0.0217

 = ¿ = 0.0217 moles
1 1 1
 mAspirin (theoretical) = n × M = 0.0217 × 180 = 3.906 g
Experimentally:
Mass of empty filter paper = 0.99g
m total = m empty filter paper+ product formed = 10.15 g
 m experimental of aspirin = 10.15 – 0.99= 9.16 g
mass experimental 9.16 g
 %yield = × 100 = ×100 = 234.511%
mass theoretical 3.906 g
 Qualitative Observation: FeCl3 is a test to detect the presence of phenols.
Tested Compound Result Color
Aspirin Negative Transparent color/ only
white solid in transparent
liquid
Salicylic acid Positive purple color