4-Methoxy-3-nitrophenyl acetate (1.06 g, 5 mmol) was dissolved in ethanol (20 mL) at 0 °C and 1N aqueous sodium hydroxide solution (5.5 mL) was slowly added. The reaction mixture was stirred at room temperature for 2 hours. Upon completion of the reaction, the reaction was quenched with acetic acid and subsequently extracted twice with ethyl acetate. The organic layers were combined, washed sequentially with water and saturated saline, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to afford the crude product 4-hydroxy-2-nitroanisole (840 mg, quantitative yield). Thin layer chromatography (TLC) showed an Rf value of 0.59 (ethyl acetate: hexane= 3:7). NMR hydrogen spectrum (400 MHz, CDCl3) data were as follows: δ 3.91 (s, 3H), 6.99 (d, 1H, J = 9.04Hz), 7.17 (dd, 1H, J = 9.04,3.00Hz), 7.38 (d, 1H, J = 3.04Hz).
