Preparation of Aspirin

Aim: The objects of the experiment are to prepare a sample of aspirin and to
purify it by recrystallisation.

Theory:
Aspirin is the world’s most widely used drug; more than 25 million kilograms
are produced annually! Aspirin is a trade name for acetylsalicylic acid. It has
long been known as an excellent analgesic, antipyretic (temperature-lowering)
and anti-inflammatory agent, and is still finding new uses, e.g. it lowers the
risk of heart attacks and strokes. Although its antecedents can be traced to
herbal remedies used as far back as ancient Greece, it was first synthesised
in pure form in 1897 by chemists at the German company Bayer, and
commercial production began in 1899.
Uncertainty surrounds the identity of its “inventor”. Aspirin was actually
prepared by a chemist called Felix Hoffmann, but recent scholarship suggests
that the idea may have come from his boss Arthur Eichengrün. Eichengrün
was Jewish and his contribution appears to have been erased during the Nazi
years. He was sent to a concentration camp in 1944, at the age of 76, but
survived and eventually died in 1949.

The Reaction:
Aspirin is the acetyl ester of a phenol called salicylic acid. Acetylation of an
alcohol or phenol can be carried out with a variety of acid or base catalysts,
and in this experiment we will use acetic acid. It is important that the
apparatus should be scrupulously dry because a small amount of water will
reverse the reaction, to reform the reactant. The product, a typical organic
compound, is insoluble in water and is isolated by precipitation from water.
In this experiment, salicylic acid participates in an esterification reaction
through its phenolic hydroxyl group, producing a compound more commonly
known as aspirin.

Method:
1. To a 125ml conical flask, add 2.0g of salicylic acid and 4ml of acetic
anhydride.

2. To this mixture add 3 or 4 drops of conc. sulphuric acid and swirl to mix.

3. After the mild exothermic reaction has taken place, warm the mixture at
~50°C on a hot water bath for about 5 minutes.
4. Cool the mixture to room temperature, and add 40ml of water. Swirl or stir
the mixture until only a single liquid phase is present.

5. Collect the resulting solid acetylsalicylic acid by suction filtration.

6. Recrystallise the solid from water. Place the solid into a conical flask and
add a small amount of boiling water, dropwise until the solid dissolves. Heat
the solution and using a glass rod, stir until small crystals appear. Filter the
solution by suction.

7. Dry in the oven. Measure the melting point of your product.

Results:
Theoretical yield ……………………… g

Yield ……………………… g

……………………… %

Melting Point ……………………… °C

Literature Melting Point ……………………… °C

Questions:
1. Acetic anhydride, instead of acetic acid, is used in this esterification.
Draw the structure of acetic anhydride, and give the mechanism of the
reaction.

2. What method (other than melting point determination) could be used to

check the purity of your aspirin product?

3. Aspirin tablets are acetylsalicylic acid pressed together with a small

amount of inert binding material usually starch. How could you test for
the presence of starch in a commercial aspirin tablet?