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

Participants

Reaction Steps

Commercially available 2-hydroxy-4-methylbenzoic acid (1.5 g, 10.0 mmol) and cesium carbonate (13.0 g, 40.0 mmol) were placed in a reaction vessel, and then N,N-dimethylformamide (40 ml) and methyl iodide (2.5 ml) were added thereto. The resulting mixture was stirred at room temperature for 5 hours. The reaction solution was filtered through celite and washed with ethyl acetate (300 ml). The filtrate was sequentially washed with water (100 ml) and a saturated aqueous sodium chloride solution (200 ml). Then, the filtrate was dried over anhydrous sodium sulfate, and concentrated under reduced pressure to yield 2-methoxy-4-methylbenzoic acid methyl ester (1.4 g) as a pale yellow oily material.

Provenance & Evidence