2-Methyl-5-nitrobenzoic acid → (2-Methyl-5-nitrophenyl)methanol

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To a solution of 2-methyl-5-nitrobenzoic acid (3.0 g, 16.6 mmol, Acros) in THF (60 ml) at ambient temperature under nitrogen was added dropwise 1.0 M borane-tetrahydrofuran complex (33.1 ml, 33.1 mmol, Aldrich). The solution was heated to 80° C. for 1.5 h. To the solution at ambient temperature was slowly added methanol (20 ml) and then heated to 80° C. for 30 min. The solvent was removed in vacuo to leave an oil. The residue was dissolved in methanol (approximately 30 ml) and the solvent removed in vacuo to give (2-methyl-5-nitrophenyl)methanol as a yellow solid (3.18 g).

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