Water → 2-Methyl-2-phenylpropanal

Participants

Reaction Steps

To a solution of oxalylchloride (4.1 ml) in dichloromethane (100 ml) was added dropwise a solution of dimethylsufoxide (7.14 g) in dichloromethane (10 ml) at -60° C., and the mixture was stirred for 10 minutes. To the resultant mixture was added a solution of 2-methyl-2-phenylpropanol (6.16 g) in dichloromethane (15 ml) at the same temperature. After stirring for one hour, to the mixture was added triethylamine (20.7 g). The mixture was further stirred for 30 minutes and allowed to room temperature. After adding water, the mixture was extracted with dichloromethane. The extract was washed with a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resultant residue was subjected to silica gel (40 g) column chromatography and elution with 2% ethyl acetate hexane solution gave 4.93 g of 2-methyl-2-phenylpropanal.

Provenance & Evidence