Synthesis of Methyl Salicylate

Fuentes, C.K.A ,Gales, B.T.B , Gepulango, E.P.A. ,Hernandez, M.R., Lantion, E.A.S.
University of Santo Tomas: Faculty of Pharmacy
Group 4 3F Pharmacy Pharmaceutical Chemistry 2 Laboratory

ABSTRACT
Methyl Salicylate was synthesized through esterification of salicylic acid with methanol in the presence of sulfuric acid,
H2SO4, which serves as dehydrating agent. Heat was involved in the esterification process until a mint odor was
obtained. The purpose of this experiment was to synthesize methyl salicylate from salicylic acid and to illustrates the
properties of organic synthesis

INTRODUCTION In this reaction, the reactants undergo a

Salicylic acid is a phenolic acid, indicating it has
two functional groups on the benzene
ring, an -OH group and a -COOH group while
Carboxylic acids react with alcohols in the
presence of an acid catalyst to produce esters.
Esters are classes of organic compounds with
strong, pleasant smell and taste. They
compromise an acid, in which hydroxyl groups
are replaced by an alkoxy group. They are
usually produced through a condensation reaction
of an alcohol and a carboxylic acid, in a presence
of a strong acid catalyst.
transesterification which is when an ester reacts
with an alcohol to form a new ester.
Transesterification is a crucial mechanism in the
formation of various products such as biodiesel
fuels which is an alternative fuel source. Animal
fat or vegetable oil contains triglyceride, an ester,
which undergo transesterification to form
glycerol, the by-product, and methyl ester.
Methyl salicylate is an organic ester easily
recognized by its odor and is known as oil of
wintergreen and involves a reaction of the -COOH
group of salicylic acid. It can be used
commercially as an antipyretic, an analgesic, or
as a non-steroidal anti-inflammatory drug
(NSAID). Methyl salicylate has a pale yellow color
and produces a mint odor ; thus, it can also be
used as a fragrance for liniments, as well as a
flavouring agent for chewing gums and mints.

Methyl salicylate can be produced through

Figure 1
Figure 1. This reaction shows esterification,
since the product of the reaction is an ester,
a compound containing the CO2R group
esterification of salicylic acid with methanol in the
presence of an acid catalyst, particularly sulfuric
acid, providing a large amount of Hydrogen ions
and speeding up the rate of reaction.

Fischer esterification is when a carboxylic acid EXPERIMENTAL

reacts with excess alcohol and a strong acid to
produce an ester. The reaction is reversible, but
the production of ester is favored with a large
presence of alcohol. This mechanism is a
common method used to produce esters and is
essential in processes such as wine aging. During
wine aging, the organic acids and ethanol in wine
undergo Fischer Esterification to create esters
that contribute to the final aroma and taste of the
wine.
A. Materials
Hard glass test tubes, 10-mL graduated cylinder,
dropping pipette, stirring rod, thermometer
Compounds tested(or samples used)
Salicylic acid, Methyl alcohol, Sulphuric acid
B. Procedure
In a hard glass test tube, 5ml of methyl alcohol
was added to a 1 gram of salicylic acid. 3 drops
of concentrated sulphuric acid was added and
then it was stirred until salicylic dissolved. The
hard glass test tube was placed on a water bath
that was maintained at 70˚C for 15 minutes until http://www.roanoke.edu/Chemistry/CSteechler/c
a mint odor was observed. hem_112/aspirin_experiment.PDF

http://safegardmedical.ca/Methyl%20Salicylate.p
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RESULTS AND DISCUSSION
When salicylic acid reacts with methanol in the
presence of an acid catalyst, methyl salicylate, or
oil of wintergreen, is produced according to the
following equation:

Figure 2

Figure 2. Illustrates the formation of methyl

salicylate by the acid catalysed reaction of
salicylic acid with methanol.

Methyl salicylate produces a minty odor after it

was placed in a water bath for 15 minutes. It is a
liquid at room temperature (mp = -9°C) and is
relatively insoluble in water. It is also quite toxic
(average lethal dose for adults is 30 mL).

Ester chemistry is of great importance in the

organic chemistry field. Methyl salicylate or
evergreen oil is a component in many products
because of its pleasant fragrances. Moreover,
Transesterification and Fischer Esterification are
crucial in the synthesis of some vital chemicals.

REFERENCE

http://www.biologie.uni-hamburg.de/b-
online/library/newton/Chy251_253/Lectures/Acyl
Substitution/AcylSubstitution.html

http://myweb.brooklyn.liu.edu/lawrence/che4x/e
6aspirin.pdf

htpp://www.nhs.uk/medicine-
guides/pages/MedicineOverview.aspx?medicine=
Methyl%20salicylate/Menthol/Camphor

http://otcsafety.org/en/ingredients/methyl-
salicylate/