Aspirin can be synthesized from salicylic acid

Aspirin also known as is acetylsalicylic
acid, can be synthesized from salicylic acid acetylsalicylic acid, and acetic
anhydride. Aspirin has a very unique structure that comprises of three chemical
groups – an aromatic ring, an ester group, and a carboxylic acid group. Aspirin is
important because it is one of the most widely used medication. In the early
years of its discovery, it was thought to just reduce the feverish symptoms of
malaria. However, in later years, chemist found out that aspirin also
alleviates the symptoms of acute rheumatism thus it was ultimately found to be
a powerful analgesic (pain reliever), antipyretic (fever reducer), and anti-inflammatory
(reduces swelling).

Although the fundamental idea
of how aspirin came about was first introduce in 1763, the breakthrough came
about in 1893, when Felix Hofmann; a chemist for the German firm of Bayer
devised a practical route for synthesizing acetylsalicylic acid. This was a breakthrough
in the history of the aspirin due to the fact that this new way of synthesizing
acetylsalicylic acid help reduces the high degree of mucosal-membrane
irritation and the highly objectionable taste without losing any of it
medicinal properties.

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Aspirin can be synthesized
from salicylic acid, acetylsalicylic acid and acetic anhydride. The reaction
undergoes nucleophilic substitution and protonation. It is the same reaction
that we have studied in class. This relation will help explain how the hydroxyl
group on the benzene ring of salicylic acid acts as the nucleophile and attacks
the electrophile site in the acetic anhydride. The reaction requires the
presence of a strong acid to act as a catalyst. In this experiment, Phosphoric
acid was used as the catalyst. When the reaction is complete, byproducts such
as unreacted starting materials and acetic acid will be present with the
desired product. Recrystallization technique will be used to purify the
product. The final product will be tested for the presence of unreacted salicylic
acid by running a test for phenols, a hydroxyl group on a benzene ring.

The objective of this lab
is to synthesize aspirin and perform a purity test on the product. To conclude,
the objective is to isolate pure acetylsalicylic acid, the synthesized product
will then be compared against a pure acetylsalicylic acid by measuring it
melting point and doing the ferric chloride test. The active ingredient of the
drug aspirin, acetylsalicylic can be synthesized through a nucleophilic substitution
reaction between salicylic acid and acetic anhydride. This type of interaction
involves a reaction of a carboxylic acid with an alcohol. The products of the
reaction are acetylsalicylic acid and acetic acid. We can subsequently hypothesis
that if the substitution reaction is done right, the reaction will produce
aspirin and acetic acid (the byproduct). This can be proven by measuring it
melting point and testing it against ferric chloride.

reaction is a general reaction in which two reactants, an alcohol and an acid,
form an ester in the final product. This reaction can be used to synthesize
aspirin from salicylic acid. These types of reaction are typically reversible,
so most of these reactions are equilibrium reactions. Le Chatelier’s principle
is a pillar of modern chemistry that states that any change imposed on a system
that is in equilibrium will cause the system to adjust to a new equilibrium in
order to counteract the change. The reaction is slow in pure acetic anhydride,
therefore phosphoric acid was used as a catalyst for the reaction because it is
a strong acid. According to Le Chatelier’s principle, this mechanism would
cause the reaction to favor the product side (aspirin and acetic acid).