Quinone → 4-Hydroxy-4-trifluoromethyl-2,5-cyclohexadien-1-one

Participants

Reaction Steps

A mixture of 74 mg (1.3 mmol) of ground ammonium bifluoride (NH4HF2), 119 mg (1.1 mmol) of 1,4-benzoquinone, and 2 mL of acetonitrile was treated with 239 mg (1.3 mmol) of triethyltrifluoromethylsilane and stirred vigorously at room temperature for 4 hours. The mixture was filtered and the filter cake was washed with dichloromethane. Concentration of the combined filtrates gave a black solid which was triturated with dichloromethane. The resulting mixture was filtered and the filter cake was washed with dichloromethane. Concentration of the combined filtrates afforded a brown solid which was purified by PTLC (one 2 mm silica gel plate eluted with a 2% methanol-98% dichloromethane) to give 83 mg (42% yield) of 4-hydroxy-4-tri -fluoromethyl-2,5-cyclohexadien-1-one.

Provenance & Evidence