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SYNTHESIS OF METHYL SALICYLATE

Berba, E. S, Calderon, K. D., Cayabyab, K. M., Cosare, S. M., Delos Santos, A. I.

Univeristy Of Santo Tomas Faculty Of Pharmacy

Abstract

Background of the Study

An ester is a compound that is formed

Methyl salicylate is a clear, colorless liquid having a characteristic wintergreen

when carboxylic acid (-COOH) reacts with

odor

or minty odor.

It

is

liquid at room

an alcohol (-OH) because carboxylic acids

temperature and has a boiling point of 222 o

have electrophilic carbons [1] .

C

and a melting point

 

of

9 o C.

It

is

also

SYNTHESIS OF METHYL SALICYLATE Berba, E. S, Calderon, K. D., Cayabyab, K. M., Cosare, S. M.,

Figure 1: Esterification

Esters tend to be volatile and have inviting aromas and fragrances of flowers and fruits. Methyl salicylate is an ester. It is the product of the esterification of salicylic acid with methanol in the presence of an

acid catalyst (conc. Sulfuric acid).

SYNTHESIS OF METHYL SALICYLATE Berba, E. S, Calderon, K. D., Cayabyab, K. M., Cosare, S. M.,

Figure 2: Esterification of Salicylic acid with methanol

slightly soluble in water (1875 mg/l at 25 °C). Methyl salicylate is also called Benzoic acid,2-hydroxy-,methyl ester; 2-

carbomethoxyphenol;

2-hydroxybenzoic

acid, methyl ester; methyl 2-

hydroxybenozate;

salicylic

acid,methyl

ester; synthetic sweet birch oil; synthetic

tea-

berry

oil;

betula

oil;

synthetic

wintergreen oil. Methyl salicylate is a fragrance ingredient used in many fragrance compounds. It may be found in fragrances

used in decorative cosmetics, fine

fragrances, shampoos, toilet soaps and other toiletries as well as in non-cosmetic products such as household cleaners and detergents. Its use worldwide is in the region of 10100 metric tonnes per annum [2] . Methyl salicylate is also used to treat

minor aches and pains of the muscles/joints (e.g., arthritis, backache, sprains). Methyl salicylate is known as a counterirritant. They work by causing the skin to feel cool and then warm. The objectives of the experiment are to synthesize methyl salicylate from salicylic acid and to observe the odor.

Methods

Materials The materials used are hard glass test tubes, 10-ml graduated cylinder, dropping pipettes, stirring rod and thermometer. The reagents used were salicylic acid, methyl alcohol and sulfuric acid. Procedure The researchers weighed 1g of salicylic acid using an analytical balance. The salicylic acid was placed into the hard glass test tube and 5ml of methyl alcohol was added. In the hard glass test tube, 5 drops of concentrated sulfuric acid was carefully added and was stirred together with methanol and salicylic acid until it formed a homogenous mixture. After mixing, the test tube was placed in a prepared water bath at 70 o C for 15 minutes. After water bath, the odor was observed.

Results and Discussion

After the 15minutes water bath, methyl salicylate was produced and it has a strong minty odor. When carboxylic acids undergo esterification it produce liquid esters in which are known to have fruity odor. The minty odor of methyl salicylate is due to it being an ester. The salicylic acid reacts with methanol and heated in the presence of acid catalyst, which is sulfuric acid; the methyl salicylate or betula oil is produced.

Reference

[1]

oc

[2]Lapezynski A., Jones L., McGinty D.,

Bhatia S., Letizia C., Api A. (2007)

Fragrance material review on methyl

salicylate. 50 Tice Boulevard, WoodcliLake, NJ 07677, USA; Elsevier Ltd.