Acetic Anhydride → 2-Methyl-5-nitrophenyl acetate

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To a mixture of 2-methyl-5-nitrophenol (2.5 g, 16.3 mmol) and 1M aqueous sodium hydroxide (24.5 ml) at ambient temperature was added acetic anhydride (1.9 ml 120.3 mmol). The mixture was stirred for 40 minutes, the solid was removed by filtration and the filtrate was extracted with ethyl acetate. The organic layers were combined, washed with an aqueous saturated sodium chloride solution, dried (MgSO4) and the volatiles were removed by evaporation to yield 2-acetoxy-4-nitrotoluene (3.1 g, 100%). A mixture of this material (3.1 g, 15.9 mmol) and 10% palladium-on-charcoal catalyst (0.12 g) in ethyl acetate (50 ml) was stirred at ambient temperature under hydrogen for 2 hours. The catalyst was removed by filtration and the volatiles were removed by evaporation to give 3-acetoxy-4-methylaniline (2.45 g, 94%).

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