Methanol → Methyl 3-chloro-4-hydroxybenzoate

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To a solution of 3-chloro-4-hydroxy-benzoic acid (1.0 g, 5.8 mmol) in methanol (30 mL) was added sulfuric acid (3 mL, 56.3 mmol) and the mixture was stirred at 60° C. for 12 hours. The reaction mixture was cooled to room temperature and the methanol was removed in vacuo. The residue was partitioned between a saturated solution of K2CO3 and ethyl acetate (3×30 mL), dried, filtered and concentrated in vacuo to yield methyl 3-chloro-4-hydroxy-benzoate (0.9 g, 83%) as a white solid. ESI-MS m/z calc 186.5. Found 187.5 (M+1)+; Retention time: 1.17 minutes (3 min run). 1H NMR (400.0 MHz, CDCl3) δ 8.05 (d, J=2.2 Hz, 1H), 7.90-7.87 (dd, J=8.8, 2.2H, 1H), 7.06 (d, J=8.8 Hz, 1H) and 3.90 (s, 3H).

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