Sulfuric Acid → Methyl 3-hydroxy-2-methylbenzoate

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Reaction Steps

A solution of 3-hydroxy-2-methylbenzoic acid (5 g, 33 mmol) and concentrated sulfuric acid (3 mL) in methanol (300 mL) was stirred at reflux for 48 hours. The mixture was cooled to room temperature and the pH was adjusted to 7 using solid sodium bicarbonate. Some methanol was evaporated and residue was partitioned between saturated aqueous sodium bicarbonate and ethyl acetate. The organic portion was washed with brine then dried over anhydrous sodium sulfate. Filtration and concentration afforded 5.3 g, 32 mmol (97%) of methyl 3-hydroxy-2-methylbenzoate. 1H NMR (400 MHz, CDCl3): 7.41 (d, 1H), 7.13-7.09 (m, 1H), 6.94 (d, 1H), 3.89 (s, 3H), 2.46 (s, 3H). MS (EI) for C9H10O3: 167 (MH+).

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