Methanol → 4-tert-Butyl-2-chlorophenol

Participants

Reaction Steps

To a solution of 4-tert-butyl-phenol (40.0 g, 0.27 mol) and SO2Cl2 (37.5 g, 0.28 mol) in CH2Cl2 was added MeOH (9.0 g, 0.28 mol) at 0° C. After addition was complete, the mixture was stirred overnight at room temperature and then water (200 mL) was added. The resulting solution was extracted with ethyl acetate. The combined organic layers were dried over anhydrous Na2SO4, filtered and concentrated under vacuum. The residue was purified by column chromatography (Pet. Ether/EtOAc, 50:1) to give 4-tert-butyl-2-chloro-phenol (47.0 g, 95%).

Provenance & Evidence