Acetic Anhydride → 2-Methyl-5-nitrophenyl acetate

関与物質

反応手順

Acetic anhydride (1.9 ml, 20.3 mmol) was added to a mixture of 2-methyl-5-nitrophenol (2.5 g, 1 6.3 mmol) and 1 M aqueous sodium hydroxide (24.5 ml) at ambient temperature. The mixture was stirred for 40 minutes, the solid was removed by filtration and the filtrate extracted with ethyl acetate. The combined organic extracts were washed with brine, dried (MgSO4) and the solvent removed by evaporation to give 2-acetoxy4-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 at 1 atmosphere pressure for 2 hours. The catalyst was removed by filtration through diatomaceous earth and the solvent removed from filtrate by evaporation to give 3-acetoxy-4-methylaniline (2.45 g, 94%).

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