General procedure for the synthesis of 2-methoxy-3-nitrophenol and 6-methoxy-2-nitrophenol from guaiacol: Fuming HNO3 (0.34 mL, 0.008 mmol) was slowly added dropwise to a solution of 2-methoxyphenol (0.886 mL, 0.008 mmol) dissolved in anhydrous dichloromethane (10 mL) at -20 °C. The reaction mixture was stirred continuously for 2 hours at room temperature. Subsequently, the reaction mixture was concentrated under reduced pressure to remove the solvent. Separation by column chromatography (eluent ratio 10-30% ethyl acetate/hexane) afforded the target products 2-methoxy-3-nitrophenol (400 mg, 29% yield) and 6-methoxy-2-nitrophenol (400 mg, 29% yield).
