PW of Organic chemistry

Unit 9: Hemi synthesis of methyl-salicylate

 Synthesis of synthesis of methyl-salicylate

Objective :
1. Understand of preparation of methyl-salicylate
2. Understand and able to use distillation reflux in organic chemistry
synthesis
 Synthesis of methyl-salicylate (Distillation reflux)

I. Introduction
➔ We’ll synthesize methyl salicylate by reacting methanol with aspirin, which
is much easier to come by than salicylic acid

➔ Methyl-salicylate :
- Main ingredient for balm andOil of Wintergreen

➔ Distillation reflux :
- allow continuous return of the volatile materials to the flask
- no solvent or reactant is removed or lost
 Synthesis of methyl-salicylate (Distillation reflux)

II. Procedure
- Acetylsalicylic acid ( ester) can break down to salicylic acid by acid or base
catalysis and fischer esterification of salicylic acid by MeOH concentrated
sulfuric acid as the catalyst
 Synthesis of methyl-salicylate (Distillation reflux)

II. Procedure
➔ Chemicals Required :
- Aspirin: 13g
- MeOH : 100ml
- H2SO4:10 ml
- Saturated Na2CO3 (3.9G/50ml):50 ml

➔ Procedure of synthesis
- Add Aspirin 13g in MeOH = 100 ml in balon
- Add H2SO4:10 ml to the reaction vessel and swirl to mix the solutions
- Allow the reaction to proceed ( 600c), stirring the reaction mixture
occasionally, for 60 minutes
 Synthesis of methyl-salicylate (Distillation reflux)

II. Procedure
➔ Purify
- Pour the contents of the reaction flask into the sep funnel.
- Add about 50 mL of ice cold tap water to the sep funnel, cap the
funnel, and agitate the contents vigorously for 30 seconds.
- Allow the contents of the sep funnel to separate into two layers.
- Retain the organic layer in the sep funnel
- Add about 50 mL of sodium bicarbonate solution to the sep
funnel, cap the funnel, and agitate the contents vigorously for 30
seconds
- Allow the contents of the sep funnel to separate into two layers
- Retain the organic layer in the sep funnel
 Synthesis of methyl-salicylate (Distillation reflux)

II. Procedure
➔ Identify :
- Physical Parameters :
● Appearance : Colorless liquid , sweet,
rooty
● Boiling point : 2220C
● d ~ 1.1825g/ml
● Solubility
Water : immiscible
Miscible in organic solvents
References
- A microscale Approach to organic laboratory techniques , Donald
th
L.Pavia,Gary M. Lampman ,5 edition
- Experimental Organic Chemistry : A Miniscale and Microscale
th
Approach, John C. Gilbert ,Stephen F.Martin ,5 edition
th
- Quantitative Chemical Analysis 7 edition , Daniel C.Harris.
- Introduction to Laboratory techniques , Pavia Kriz ,Lampman Engel ,
1998
rd
- Techniques in Organic Chemistry , 3 edition , Jerry R.Mohrig ,
Christina Noring Hammond Paul F.Schatz