Dimethyl Sulfoxide → 2-(4-Chlorophenyl)-2-methylpropanal

Participants

Reaction Steps

To a stirring solution of oxalyl chloride (1.422 mL, 16.25 mmol) in 40 mL of dichloromethane at −5° C. was added dimethylsulfoxide (1.153 mL, 16.25 mmol) dropwise. After 15 min of stirring, a solution of 2-(4-chlorophenyl)-2-methylpropan-1-ol (1.0 g, 5.42 mmol) in 15 mL of dichloromethane was added dropwise and the resulting mixture was stirred for 30 min at the same temperature. Then triethylamine (3.02 mL, 21.66 mmol) was added and the resulting mixture was stirred for 1 hr at −20° C. with gradual warm-up to room temperature over 2 hrs. The reaction was quenched with water and extracted with ether. The organic layer was separated and washed with brine. It was then dried over anhyd. magnesium sulfate, concentrated and chromatographed using silica gel flash chromatography to yield 2-(4-chlorophenyl)-2-methylpropanal (0.82 g, 4.49 mmol, 83% yield) as a clear oil. 1H NMR (400 MHz, CDCl3) δ ppm 9.48 (1H, s), 7.33-7.39 (2H, m), 7.21 (2H, d, J=8.79 Hz), 1.46 (6H, s).

Provenance & Evidence