Acetic Acid → 4-(Trifluoromethyl)phenol

Participants

Reaction Steps

A solution of 200 mg (1.1 mmol) of 4-hydroxy-4-trifluoromethyl-2,5-cyclohexadien-1-one in 1 mL of absolute ethanol was treated successively with 147 mg (2.2 mmol) of zinc dust and 1 mL of a solution of 80% acetic acid--20% water. The mixture was heated to reflux for one hour, allowed to cool to room temperature, and poured into 20 mL of water. The resulting aqueous mixture was extracted with three 10 mL portions of diethyl ether. Combination, extraction with one 10 mL portion of 10% Na2CO3, drying (MgSO4), and concentration of the ether layers afforded a residue which was subjected to PTLC (one 2 mm silica gel plate eluted with dichloromethane), giving 151 mg (83% yield) of 4-trifluoromethylphenol.

Provenance & Evidence