Synthesis

of
Aspirin

O R G A N I C C H E M I S T R Y
History
First synthesized by Charles Gerhardt in 1853 from salicylic acid and
acetic anhydride

In 1893, Felix Hoffmann (Bayer company in Germany) reinvestigated

the synthesis reported by Gerhardt forty years earlier

Bayer Company obtained a patent on acetylsalicylic acid

Bayer coined the name Aspirin for their new product to reflect its
acetyl nature and its natural occurrence in the Spiraea plant

O R G A N I C C H E M I S T R Y
Biological Activity
Analgesic - painkiller

Antipyretic - fever reducer

Anti-inflammatory - inhibition of the

synthesis of prostaglandins

Uricosuric - enhances the elimination

of uric acid

O R G A N I C C H E M I S T R Y
Materials and Reagents
Hexane
Methanol Vacuum flask
Distilled H2O Büchner funnel
Salicylic acid
Acetic Anhydride
Concentrated H2SO4

O R G A N I C C H E M I S T R Y
 Procedure

Selection of
recrystallizing
solvent Purification

Synthesis

O R G A N I C C H E M I S T R Y
Properties of a Recrystallizing Solvent
The compound should be very soluble at the boiling point of the solvent
and only sparingly soluble in the solvent at room temperature.

The unwanted impurities should be either very soluble in the solvent at

room temperature or insoluble in the hot solvent.

The solvent should not react with the compound being purified.

The solvent should be volatile enough to be easily removed from the

the compound after it has crystallized.

O R G A N I C C H E M I S T R Y
Recrystallization – Purification method
Rapid and convenient way of purifying a solid
organic compound

The material to be purified is dissolved in the

hot appropriate solvent

As the solvent cools, the solution become

saturated with respect to the substance, which
then crystallize

Impurities stay in solution

O R G A N I C C H E M I S T R Y
Assessment of Result
Examine the following:

Physical appearance – physical state, color, odor, texture, etc.

Melting point – determine the melting point range

Percent yield – calculate the yield of the reaction based on the experimental
result and stoichiometry of the reaction

Infrared spectra – identify the functional groups present in the spectra and
compare the obtained spectrum with the reference spectrum

O R G A N I C C H E M I S T R Y
Assessment of Result
Melting point
the melting point of a compound is a criterion for purity as well as for
identification.
pure, nonionic, crystalline organic compound usually has a sharp and
characteristic melting point.
very small amounts of miscible impurities will produce a depression of
the melting point and an increase in the melting point range.

acetylsalicylic acid: 136-138°C

O R G A N I C C H E M I S T R Y
Assessment of Result
Percent yield

Experimental yield: determine experimentally

Theoretical yield: calculated from the limiting reagent
Percent yield if the actual yield is 1.79 g:

O R G A N I C C H E M I S T R Y
Assessment of Result
A
IR Analysis

O R G A N I C C H E M I S T R Y
 Assessment of Result
Classification Tests:
Hydroxamic acid Test
REAGENTS: hydroxylamine, KOH, HCl and FeCl3
POSITIVE FOR: Esters
POSITIVE RESULT: magenta or red-brown solution
REACTION: Nucleophilic substitution
 Assessment of Result
Classification Tests:
Ferric Chloride Test
REAGENTS: FeCl3
POSITIVE FOR: Phenols
POSITIVE RESULT: wine red solution
REACTION: Complex formation
Exercise
Two organic compounds A&B with molecular formula, C8H8O2. Both compounds
showed a C=O stretch in the IR spectrum. Using chemical analysis, Both
compounds yielded yellow ppt with H2SO4-HNO3 reagent. Compound A gave
wine red solution with FeCl3 while compound B afforded a magenta solution
with hydroxylamine and FeCl3. Draw the structure of compound A and B.