Synthesis of Methyl Salicylate

Silverio, A. Soriano, R. Tan, J. Tequillo H. Tolentino M.

University of Santo Tomas Faculty of Pharmacy

Abstract: Performed in this experiment was synthesis of Methyl salicylate from aspirin. During the said activity, the
commercially available aspirin was compounded to be used as the source of the acetylsalicylic acid, which is much
easier to come by than salicylic acid, and performed esterification, where a condensation reaction between an
alcohol and an acid, typically in the presence of a strong acid catalyst, such as sulfuric acid. Water bath of 5-10
minutes with maintained temperature of 70C was done; strong minty odor of the ester was observed and indicated
the complete synthesis of methyl salicylate, also known as Oil of Wintergreen


I. Background
Esters are a class of organic compounds. An ester compromises an organic or inorganic acid in
which one or more hydroxy (OH) groups have been replaced by and alkoxy(O-alkyl) group. For
example, the simplest ester, methyl formate (CHO-OCH3), is made up of formic acid (CHO-OH) in
which the hydroxyl group has been replaced by a methoxy group (OCH3).
Similarly, ethyl acetate (CH3CO-OCH2CH3) is made up of acetic acid (CH3CO-OH) in which the
hydroxy group has been replaced by an ethoxy group (-OCH2CH3) Although esters can be produced
by many mechanisms, the most commonly used method is called esterification, which is a
condensation reaction between an alcohol and an acid, typically in the presence of a strong acid
catalyst, such as sulfuric acid. For example, ethyl acetate can be produced by reacting ethanol (ethyl
alcohol) with acetic acid and isopropyl butyrate by reacting isopropanol (isopropyl alcohol) with butyric
acid. Esters were traditionally named by combining the name of the alcohol with the root name of the
acid and adding ate as a suffix. Traditional names are still widely used by most chemists,
particularly for the simple esters. The IUPAC naming system uses the systematic names for the
alcohol and root name of the acid, followed by oate. For example, the traditional name n-amyl
acetate (n-amyl alcohol with acetic acid) is represented in IUPAC nomenclature as 1-pentyl ethanoate
(1-pentyl alcohol, the systematic name for n-amyl alcohol, with ethanoic acid, the systematic name for
acetic acid). Esters typically have strong, often pleasant, scents and tastes, so many esters are used
as flavorings and perfume agents, either individually or in combination For example, the scent and
taste of strawberries is due to the presence of (among others) methyl cinnamate, ethyl butyrate, ethyl
caproate, isobutyl acetate, and benzyl acetate.

II. Materials and Method

a. Apparatus
Hard Glass Test Tubes
10mL Graduated Cylinder
Dropping pipette
Stirring rod
Thermometer

b. Reagents
Salicylic acid
Methyl alcohol
Sulphuric acid

c. Method
1. Salicylic acid was weighed 1 gram then was transferred to a hard glass test tube
2. 5mL of methyl alcohol was added
3. 3 drops of Concentrated Sulfuric acid was carefully added in the solution
4. The Salicylic acid was stirred until completely dissolved.
5. Test tube was placed on a water bath with maintained temperature of 70C for 15
minutes
6. The odor of the solution was recorded.

III. Results

The solution has an odor of strong mint odor.


IV. Conclusion

The reaction of Salicylic acid to Methyl Alcohol is shown in figure number 1.

Figure 1. Reaction of Salicylic acid to Methyl Alcohol

This reaction can give therapeutic effects that treat minor aches and pains of the
muscles/joints (e.g., arthritis, backache, sprains). Menthol and methyl salicylate are
known as counterirritants. They work by causing the skin to feel cool and then warm.
These feelings on the skin distract you from feeling the aches/pains deeper in your
muscles, joints, and tendons.

V. Reference

[1] Thompson, R.B. (2008). Illustrated guide to home chemistry experiments. Beijing: O'Reilly
[2] Retrieved from: Web MD, 201. http://www.webmd.com/drugs/drug-18536-methyl+salicylate-
menthol+top.aspx?drugid=18536&drugname=methyl+salicylate-menthol+top