Exercise 11

SYNTHESIS OF ASPIRIN
(Acetylsalicylic acid from Salicylic acid)

John Christian C. Quillope

Group 2
CHEM 40.1 11L

I. Introduction
Defined as the preparation of a desired organic compound from commercially available
materials, organic synthesis plays a vital role in organic chemical industry, especially in the
need of sample compounds for chemical analyses. To successfully synthesize a compound, one
must possess a wide understanding of the specific reactions undergone by specific families of
compounds, as there are reactions which seem to be flawlessly occurring from a theoretical
standpoint, although in reality, side reactions concur.
In any synthesis, one is expected to obtain a pure sample of the desired compound using
the most efficient and the most convenient method possible. This is the reason why the
reactions which will be employed in the synthesis should only yield a single product, should
not have any side reaction, and should have the fewest possible steps to avoid further errors in
the method. Minimal work is highly favoured considering the amount of time and resources
which will be used up to efficiently yield the maximum amount of the desired product.
The concept of organic synthesis has greatly helped various chemical industries,
especially in the field of medicine. One of the simplest examples of organic synthesis is the
synthesis of acetylsalicylic acid from salicylic acid. A practical way to synthesize such
compound had been discovered by a chemist named Felix Hoffman from the Bayer Company
in Germany. Under the trade name Aspirin, it was first inferred that salicylic acid was the
medically active form of it; however, it is now well established that acetylsalicylic acid is more
potent than salicylic acid in functioning as an analgesic after discovering that acetylsalicylic
acid was less of an irritant, and can be hydrolysed back to salicylic acid in the small intestine
which can be then absorbed into the bloodstream.
The synthesis of aspirin will be employed using the concept of nucleophile acyl
substitution as the basis of the experiment. The balanced chemical reaction in the synthesis is
given by:

II. Objectives
III. Materials and Methods
A. Schematic Diagram of the Procedure
B. Setup(s)
C. List of Necessary Chemicals
Name and
Structure of the
Compound

Function in the
Exercise

Physical Properties
-

IV. Data
V. Sample Calculations

appearance,
molar mass,
boiling point,
density, etc.

Hazards

Precautions

Alkyl halides have higher boiling points than their parent alkanes due to the fact that alkyl
halides have strong London-dispersion forces since they have attractive dipole-dipole forces
caused by the high electronegativities of the halide atoms attached to the alkyl halides. They also
have higher molar masses which means that the electron shell of halogens are larger than those
of hydrogen and carbon, thus having stronger attraction which would then require large amounts
of energy for those forces to be broken, thus having high boiling points.