Methanol → Methyl 4-chloro-2-hydroxybenzoate

Participants

Reaction Steps

A solution of 4-chloro-2-hydroxybenzoic acid (100 g, 0.58 mol), methanol (500 mL) and concentrated sulfuric acid (50 mL) was refluxed for 20 hr. Benzene (100 mL) was added and the solvent was slowly distilled off from the mixture until 300 mL of distillate was collected. The residue was taken up in diethyl ether, the aqueous phase was separated, the organic phase was washed with sodium bicarbonate solution, dried and evaporated to give 100 g of the title compound as an oil which crystallized on cooling; mp 27°-30° C., and IR (mineral oil) 3150, 1660 and 1600 cm-1.

Provenance & Evidence