Methanol → Benzoic acid, 2-hydroxy-3-methyl-, methyl ester

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-hydroxy-3-methylbenzoic acid (18.1 g, 119 mmol) in 70 mL of methanol is added dropwise 3.3 mL of concentrated sulfuric acid. The resulting solution is heated under reflux for 24 hours. Another 7 mL of concentrated sulfuric acid is added and the reaction is heated at 70° C. overnight. The mixture is cooled and a pink layer separated. This layer is dissolved in 200 mL of ethyl acetate and the solution is washed with saturated aqueous sodium bicarbonate and brine, dried over sodium sulfate, filtered and concentrated to give an oil which is purified by chromatography on silica gel using a mixture of 30% ethyl acetate and 70% hexane as the eluent. Methyl 2-hydroxy-3-methylbenzoate is obtained as a clear oil.

Provenance & Evidence