Experiment 11

The Synthesis of Aspirin

Introduction:
What has aspirin been known to do? It reduces headache pain (analgesic), reduces fever (antipyretic),
relieves the swelling and joint pain associated with rheumatism and arthritis (anti inflammatory),
enhancing the elimination of uric acid (uricosuric).
The starting materials are salicylic acid and acetic anhydride, both of which are easily available and
inexpensive. Our reaction becomes:
O CH3
C
OH O O O O
+ + C
OH O CH3 OH CH3 OH
C CH3 C
O O

Observe that the reaction produces a second product, acetic acid.

Water is an inappropriate solvent in which to carry out this reaction since water would destroy one of the
reactants. Since the reaction is slow in pure acetic anhydride, we use a well established catalyst for the
reaction, namely, concentrated sulfuric acid. By Le Chatelier’s principle, the presence of an excess of
acetic anhydride forces the equilibrium towards the desired product, aspirin. We also heat the solution to
accelerate the approach to equilibrium. After the reaction is complete, we can consider adding water to
the reaction vessel.

Procedure:
1. Put 1.0 g of salicylic acid and 3 mL of acetic anhydride in a dry Erlenmeyer flask, mix well and add 3
drops of concentrated H2SO4.
2. Heat a 1000-mL beaker with 150 mL of water in it to boil, put the Erlenmeyer flask in the hot bath for
about 20 min. After that, cool the flask on the table.
3. Add 10 mL of ice water drop by drop into the flask and stir well.
4. Add another 10 mL of ice water into the flask and stir well, cool it in an ice bath. After the solid
precipitation complete, suction-filter the solution.
5. Put the filter paper with solid on a watch glass, dry the solid in an oven. Weigh the solid after it’s been
dried and calculate the yield.
6. Put some salicylic acid and some of the solid you produced in a test tube respectively. Dissolve them
with 1 mL of ethanol, add 1 drop of FeCl3 into the test tube and test the result.
Results:

Weight of salicylic acid:

Crystal appearance of salicylic acid:

Weight of aspirin:

Crystal appearance of aspirin:

Yield of aspirin:

Color of salicylic acid solution with FeCl3 testing:

Color of salicylic acid solution with FeCl3 testing:

Questions:
1. The amount of aspirin you produced is bigger or smaller than the theoretic amount? Explain.
2. Why does acidic odor exist when the aspirin stored for a period of time?
3. What should we do if the solid does not form after the solution have been ice bathed?
4. Why the experiment should be operate in a water free environment?
5. Does your aspirin product have some acetic odor? Explain.
6. Please look up the references for the properties of aspirin and salicylic acid.