Methyl trifluoromethyl ketone → 1,1,1-Trifluoro-2-methyl-3-(4-benzoylphenoxy)propan-2-ol

Participants

Reaction Conditions

Reaction Steps

A suspension of trimethylsulfoxonium iodide (8.57 g, 38.9 mmol) in 50 mL of dichloromethane cooled to 0° C. was treated with a solution of KOH (2.18 g, 38.9 mmol) in water (40 ml). The ylide was treated with trifluoroacetone (4.36 g, 38.9 mmol) and the reaction was maintained at 0° C. for 0.5 hours followed by reflux for 1.5 hours. The reaction was cooled to 0° C. and treated with a solution of 4-Hydroxybenzophenone (7.72 g, 38.9 mmol), KOH (2.18 g, 38.9 mmol) in water/ethanol (40 ml/5 ml). The mixture was treated with N-benzyltrimethylammonium hydroxide (8.46 g, 50.6 mmol) and then refluxed for 18 hours. The mixture was poured into ice-water and extracted with dichloromethane. The combined extracts were dried and evaporated to yield a brown oil. Chromatography of this oil, eluting with dichloromethane/hexane/ethyl acetate provided the title compound as a white solid (1.7 g); mp 70° -73° C. NMR: 1.45 (s,3, CH3), 4.16 (q,2, CH2), 6.44 (s,1, OH), 7.16 (dd,2, J=7,2, Ar), 7.65 (m,7, Ar); MS: m/z=325(M+1). Analysis for C17H15F3O3 : Calculated: C, 62.96; H, 4.66; Found: C, 62.71: H, 4.61.

Provenance & Evidence