2-Hydroxy-p-toluic acid → Methyl 2-methoxy-4-methylbenzoate

Participants

Reaction Steps

A mixture of 2-hydroxy-4-methylbenzoic acid (7.61 g), iodomethane (15.6 ml) and potassium carbonate (17.3 g) in N,N-dimethylformamide (100 ml) was stirred at room temperature for 5 hours. The reaction mixture was filtered and the filtrate was poured into a mixture of ethyl acetate and water. The organic layer was separated, washed with water and brine, dried over magnesium sulfate and concentrated. The residue was chromatographed on silica gel column eluting with a mixture of n-hexane and ethyl acetate (4:1) to give methyl 2-methoxy-4-methylbenzoate (7.99 g) as an oil.

Provenance & Evidence