2-Hydroxy-p-toluic acid → Benzoic acid, 2-hydroxy-4-methyl-, methyl ester

Participants

Reaction Conditions

Reaction Steps

Commercially available 2-hydroxy-4-methylbenzoic acid (1.0 g, 7.0 mmol) and potassium bicarbonate (841 mg, 8.4 mmol) were placed in a reaction vessel, and then N,N-dimethylformamide (10 ml) and methyl iodide (0.65 ml, 10.5 mmol) were added thereto. The resulting mixture was stirred at 40° C. for 4 hours. The reaction solution was diluted with ethyl acetate (200 ml), and sequentially washed with water (70 ml), with a saturated aqueous sodium bicarbonate solution (70 ml), twice with water (70 ml), and with a saturated aqueous sodium chloride solution (70 ml). The ethyl acetate solution was dried over anhydrous sodium sulfate, and then concentrated under reduced pressure to yield 2-hydroxy-4-methylbenzoic acid methyl ester (1.1 g) as a pale yellow oily material.

Provenance & Evidence