1-Chloro-3,5-dimethoxybenzene → 3-Chloro-5-methoxyphenol

Participants

Reaction Conditions

Reaction Steps

To sodium methanethiolate (12.32 g, 173.80 mmol) was added 1-methyl-2-pyrrolidine (75 mL) followed by 1-chloro-3,5-dimethoxy-benzene (20.00 g, 115.87 mmol) and the reaction heated in a 140° C. bath for 2.5 hours then stirred at room temperature over night. The 1-methyl-2-pyrrolidine was removed under reduced pressure and the material partitioned between ethyl acetate/water/1N hydrochloric acid. The organic layer was washed with twice with 1N hydrochloric acid, once with aqueous saturated sodium chloride, dried over magnesium sulfate and solvent removed under reduced pressure to give a yellowish solid. The solid was chromatographed on 400 mL plug of silica gel eluting with dichloromethane. The combined purified fractions were removed of solvent to give the title compound as a yellow solid (16.62 g, 90%). 1H NMR (300 MHz, DMSO-d6) δ 6.43 (t, J=2.0 Hz, 1 H), 6.40 (t, J=1.9 Hz, 1 H), 6.28 (t, J=2.1 Hz, 1 H), 3.71 (s, 3 H); MS (APCI+) m/z 159 [M+1]+; tR=2.04 min.

Provenance & Evidence