Objective

To synthesize methyl salicylate from salicylic acid

Introduction
Methyl salicylate was first isolated in 1843 by extraction from the bush Gaultheriaprocumbens. The
berries from this bush were used medicinally by native Americans, who brewed a tea frm the leaves
to alleviate rheumatic symptoms, headache, fever, sore throat and various aches and pains. It was
soon found that methyl salicylate had analgesic (pain relieving) and antipyretic (fever reducing)
character almost identical to that of salicylic acid when taken iternally.

Methyl salicylate will be prepared from salicylic acid, which is esterified at the carboxyl group with
methanol. Esterification is an acid-catalysed equilibrium reaction. The equilibrium can be driven
toward the product side by increasing to concentrations of one of the reactants. In this experiment, a
large excess of methanol wil shift the equilibrium to favour more complete formation of the ester.

Chemicals
Salicylic acid

Methanol

Concentrated sulfuric acid

5% sodium bicarbonate solution

Anhydrous sodium sulphate

Boiling chips

Apparatus
Reflux apparatus

Separatory funnel
Procedure
1. 5 g of salicylic acid are weighed and 25 mL of metahanol was added in with swirling n a 100
ml round bottom flask ( size of the round bottom flask must fit to the condenser because we
will continue with heating by reflux). The flask was heated if possible using a heating mantle
to dissolve the acid.
2. After all the acid has been dissolved, 10 ml concentrated sulphuric acids with swirling was
slowly added into the mixture. Then, a few boiling chips was added to the flask and the
reaction flask are set for reflux in a heating mantle for about 20 minutes.
3. The reaction mixture are cooled to room temperature and the mixture was poured into a
separatory funnel.
4. The mixture was extracted with 40 ml methylene chloride and the organic layer was separated
into 100 ml conical flask.
5. The organic layer was washed with 25 ml of distilled water and the organic layer are separated.
6. 25 ml of 5% sodium bicarbonate solution was continued wash. The organic layer was drained
into a 100 ml conical flask.
7. 5 g of anhydrous sodium sulphate was added to the flask and the mixture was swirled several
times.
8. The organic layer was filter off and the solvents was evaporated using a heating mantle. The
observation and the amount of the product obtained during the experiment was recorded.
Pre-lab assignment
1. Why the mixture need to be refluxed to dissolve the acids ? why we cannot use the direct
heating
 it allows the reaction to be carried out at the boiling point of the solvent and yet it
prevent loss of solvent or reagent due to evaporation.. it is because to heat a
mixture for a long time and to be able to leave it relatively untended.

2. State the purpose of adding the boiling chips during reflux

 Boiling chips will prevent superheating of the liquid being distilled and it will cause a
more controlled boil, eliminating the possibility that the liquid in the distillation flask
will bump into the condenser.

3. State the function of methylene chloride. Suggest other chemical that can replace the
function of methylene chloride.
 Methylene chloride is used as solvent and paint remover.
 Chemical: acetone

4. State the function of 5% sodium bicarbonate solution and anhydrous sodium sulphate.
 Sodium bicarbonate can be used as a wash to remove any acidic impurities from a
"crude" liquid, producing a purer sample. Reaction of sodium bicarbonate and an
acid produces a salt and carbonic acid, which readily decomposes to carbon dioxide
and water
 anhydrous sodium sulphate is widely used as an inert drying agent, for removing
traces of water from organic solutions.

5. Draw an equation on the formation of methyl salicylate.

6. State the use of methyl salicylate

 Methyl salicylate topical (for the skin) is used for temporary relief of muscle or joint
pain caused by strains, sprains, arthritis, bruising, or backaches. Methyl salicylate
topical may also be used for purposes not listed in this medication guide.
Disscusion
The methyl salicylate is formed through a combination of transesterification and a Fischer
esterification mechanism, which involves the intermediate salicylic. The reaction begins with a
transesterification to yield salicylic acid. This intermediate goes through a Fischer esterification
involving the addition of an alcohol, which reacts with the carboxylic acid group via an acid catalyst.
Since an intermediate is formed the reaction proceeds at a much slower rate and is thermodynamically
controlled, the heat provides the energy needed for the reaction to form methyl salicylate. The
reaction ismonitored through TLC plates, as the reaction progressed, the reaction sample spot would
move further up the stationary phase since methyl salicylate is less polar. The reaction was completed
when there was only a methyl salicylate spot in the reaction lane. The extraction portion of this
experiment was an effective method as indicated by the 84.7% recovery of aspirin. The extraction
removed the aspirin compound from the binding agents, which was accomplished via the introduction
of a polar solvent. The binders are insoluble in the polar solvent, methanol, while acetylsalicylate acid
dissolves in methanol. In this experiment we have used a reflux and separatory technique that we
have been doing before in experiment 1 . These two technique was synthesize a methyl salicylate. At
the end of the experiment , the actual amount of methyl salicylate produced is 36.42 g and the percent
yield is . There was no mistakes when we are doing the experiment .

Conclusion
Methyl salicylate is an organic ester naturally produced by many species of plants, specifically
wintergreen. Its is artificially syhthesized to produce perfumes and fragrances, foods and beverages,
and liniments. The process of refluxing involves distillation with condensation of vapors and
returning these vapors t the oriinal system. This process is widely used in industrial and laboratory
distillations. Mass of methyl salicylate collected was 36.42 g . Percent yield was

References
Internet

1. http://www.chem.ucalgary.ca/courses/351/laboratory/reflux.pdf
2. https://www.roanoke.edu › documents › chemistrylabmanual › spring2012
3. https://labmonk.com › synthesis-of-methyl-salicylate
4. https://www.coursehero.com/file/28558372/Synthesis-of-Methyl-Salicylate-lab-
reportdocx/#/doc/qa

Book

1. laboratory manual of CHM207 , UiTM Arau, Perlis