Methanol → Methyl 3-hydroxy-2-methylbenzoate

Participants

Reaction Steps

A solution of 3-hydroxy-2-methylbenzoic acid (5 g, 33 mmol) and sulfuric acid (500 μl) in methanol (20 mL) was stirred at reflux for 15 hours. The reaction mixture was allowed to cool to room temperature and partitioned between water and ethyl acetate. The aqueous portion was extracted with ethyl acetate and the combined organic portion was washed with saturated sodium bicarbonate, brine, and then was dried over sodium sulfate, filtered and concentrated under reduced pressure to afford (5.46 g, 100%) of methyl 3-hydroxy-2-methylbenzoate. 1H NMR (400 MHz, DMSO-d6): 9.71 (s, 1H), 7.20-7.17 (m, 1H), 7.11-7.07 (m, 1H), 7.01-6.97 (m, 1H), 3.79 (s, 3H), 2.28 (s, 3H). MS (EI) for C9H10O3: 166 (MH+).

Provenance & Evidence