Synthesis of Aspirin from Salicylic Acid

Rosheen Angel Villaraza, Dana Young, Dana Fay Yu, Ray Allen N. Zafra*

Department of Biology, College of Science

University of Santo Tomas, Espana Street, Manila 1008

Methodology

In order to synthesize aspirin, acetic anhydride was therefore reacted with salicylic acid.
First off, 1.00 g of the said salicylic acid was placed on top of a watch glass and then weighed
with the utilization of an analytical balance and transferred into an Erlenmeyer flask. 2.00 ml of
acetic anhydride was then added into the flask subsequently succeeded by the supplementation of
concentrated sulfuric acid (H2SO4) in 5 drops.

Until the dissolution of the salicylic acid, the mixture was thoroughly mixed by using a
stirring rod. A beaker capacity filled with tap water was then boiled by use of a hot plate. Then, a
wash bottle filled with ice-cold water was prepared as well as an evaporating dish filled with ice
and cold water. A thermometer was also utilized to check the temperature of the water in order to
provide information to the user as to when to turn off the hot plate. When the water began to
boil, the hot plate was then turned off. The flask containing the acetic anhydride was then placed
inside the beaker and the contents were stirred for a minute. The mixture was subjected to the
water bath with the temperature ranging from 70-80 degrees Celsius. After the water bath, the
flask was dipped onto the evaporating dish filled with ice cold water for cooling. Thereafter, the
solution inside the flask was subjected to vacuum filtration and then subsequently placed inside a
100 ml beaker.
 Two methods of purification by recrystallization was used, one was Single Solvent
method that involved only the use of H2O and the other was the Double Solvent method that
involved Hexane/EToAc.

As for the Single Solvent method, the crude aspirin in the 100 ml beaker was put into a
20 ml beaker with boiling water thus creating a hot solution which was then placed into another
ice bath for crystallization. Vacuum filtration was again done and after it, the aspirin was dried,
weighed and put into a vial for submission. The % yield was also obtained.

As for the Double solvent method, the procedures were almost identical with the
difference lying in the substances used to treat the filter paper. Instead of water being used to wet
the filter paper, hot ethyl acetate was utilized. And again with the filter paper in the process of
vacuum filtration, instead of water, the paper was treated with cold hexane.

References:

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chromatography to the analysis of trace amounts of salicylic acid, acetylsalicylic
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Medical Journal, 329(7479), 1408.
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