Acetic Acid → Methyl 5-hydroxy-4-methoxy-2-nitrobenzoate

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To a solution of 5-hydroxy-4-methoxy-2-nitrobenzoic acid [Sinha J. Ind. Chem. Soc., 47, 925 (1970)] (83.0 g, 0.39 mol) in MeOH (250 ml) was added concentrated H2SO4 (20 ml) and the reaction mixture was heated to reflux for 16 h. On cooling, the reaction mixture was poured into aqueous potassium carbonate solution and acetic acid was added until pH 4 was reached. The mixture was extracted with chloroform, the organic layer washed twice with H2O and dried over MgSO4. Evaporation under reduced pressure afforded the subtitle compound as yellow crystals (77.0 g, 87%). Rf 0.30 (benzene/acetone 4/1, v/v); m.p. 146-9° C.

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