2-Chloro-4-methoxyphenol

935-50-2

18113-03-6

General procedure for the synthesis of 2-chloro-4-methoxyphenol from 4,4-dimethoxycyclohexa-2,5-dien-1-one: 4,4-dimethoxycyclohexa-2,5-dien-1-one (1.0 mmol) was added to the reaction vessel, followed by the addition of a solution of 1,4-dioxane in 4N HCl (0.5 mL, 2 mmol) dropwise. The yellow color of the reaction mixture faded rapidly. After completion of the reaction, the solvent was removed by vacuum evaporation. The residue was diluted with ethyl acetate (10 mL) and washed with saturated aqueous NaHCO3 solution (5 mL). The organic layer was dried with anhydrous Na2SO4, filtered and concentrated to give 2-chloro-4-methoxyphenol in 95% yield. If necessary, it can be purified by column chromatography using ethyl acetate/hexane gradient elution.