4-Methylbenzophenone → 4-Methyl-alpha-phenyl-alpha-(trifluoromethyl)benzenemethanol

Participants

Reaction Conditions

Reaction Steps

Into a dry Schlenk flask under an argon atmosphere, was added 7 mL DMF solution of phenyl trifluoromethyl sulfone (1a, 420 mg, 2 mmol) and 4-methylbenzophenone (196 mg, 1 mmol) at −50° C., was added 3 mL DMF solution of tBuOK (280 mg, 2.5 mmol). The reaction flask was then sealed and the reaction mixture was then stirred from −50° C. for 1 h, followed by stirring at −50° C. to room temperature overnight. The reaction mixture was quenched with 10 mL of ice water, and extracted with ether (20 ml×3). The combined ether phase was washed with saturated NH4Cl aqueous solution, followed by washing with water. After drying over MgSO4, the ether solvent was removed under vacuum. The crude product was further purified by column chromatography (hexanes/ether=9/1) to give 225 mg of product, 4-methyl-α-phenyl-α-(trifluoromethyl)benzenemethanol as a colorless oily liquid, yield 85%. 1H NMR (CDCl3): δ 2.36 (s, 3H); 2.89 (s, 1H); 7.17–7.51 (m, 9H). 19F NMR (CDCl3): δ −74.4. MS: 266 (M+).

Provenance & Evidence