Methanol → Methyl 2-ethylbenzoate

Reaction equation

[CH2:1]([C:3]1[CH:11]=[CH:10][CH:9]=[CH:8][C:4]=1[C:5]([OH:7])=[O:6])[CH3:2].S(=O)(=O)(O)O.[CH3:17]O>>[CH2:1]([C:3]1[CH:11]=[CH:10][CH:9]=[CH:8][C:4]=1[C:5]([O:7][CH3:17])=[O:6])[CH3:2]

Participants

Reactant 3

HCID 887Methanol

HCID 1118Sulfuric Acid

HCID 341702-Ethylbenzoic acid

Product 1

HCID 583295Methyl 2-ethylbenzoateYield 86%

Procedure

A solution of 11.8 g. (0.076 mole) of 2-ethylbenzoic acid in 25 ml. of absolute methanol is treated cautiously with 2.5 ml. of concentrated sulfuric acid and heated to reflux. After 4 hours, the mixture is poured onto ice and the oily product is extracted into ether. Evaporation of the washed (water, 5% aqueous sodium bicarbonate and water) and dried extract under reduced pressure leaves methyl 2-ethylbenzoate as the residual colorless oil in a yield of 86%.