Dimethyl Sulfoxide → (1,1'-Biphenyl)-4-carboxaldehyde

Participants

Reaction Conditions

Reaction Steps

To a solution of dimethylsulfoxide (3.9 ml, 54.4 mmol) in methylene chloride (70 ml) under nitrogen atmosphere is added trifluoroacetic acid (5.7 ml, 40.8 mmol) with stirring at -70° C. After 10 min., 4-biphenylmethanol (5 g, 27.2 mmol) is added, and after being stirred for 30 min., triethylamine (30 ml, 218 mmol) is added. The reaction mixture is allowed to warm up to r.t., diluted with water, and extracted with methylene chloride. The organic layer is washed successively with 1N hydrochloric acid and saturated sodium bicarbonate, dried over magnesium sulfate and concentrated to give 4-biphenylmethanal. To a cold solution (0° C.) of 4-biphenylmethanal in THF (50 ml) under nitrogen atmosphere is slowly added 3M phenylmagnesium bromide solution in diethyl ether (5.3 ml, 15.7 mmol) with stirring. The reaction mixture is allowed to warm up to r.t. and the stirring is continued for 15 hrs. The mixture is diluted with water and extracted with diethyl ether. The organic layer is washed with saturated ammonium chloride, dried over magnesium chloride, and concentrated in vacuo. The residue is purified by flash column chromatography on silica gel with 15% diethyl ether in hexane to give (4-biphenyl)-phenylmethanol.

Provenance & Evidence