Dimethyl Sulfoxide → 16-Methoxymethoxyhexadecanal

Participants

Reaction Steps

To a solution of 1.23 ml of oxalyl chloride in 60 ml of dichloromethane was added dropwise at -78 ° C. a solution of 2.0 ml of dimethyl sulfoxide in 2 ml of dichloromethane. After stirring for 10 minutes, a solution of 2.13 g of 16-methoxymethoxyhexadecanol in 30 ml of dichloromethane was added dropwise and the mixture was allowed to slowly rise up to -20° C. and then stirred for 15 minutes. 5.9 ml of triethylamine was added and the mixture was stirred at 0° C. for one hour. To the reaction solution was added a saturated aqueous solution of ammonium chloride and extracted with chloroform. The extract was dried over anhydrous sodium sulfate, distilled under reduced pressure and chromatographed over a silica gel column to afford the title compound as a colorless oily substance.

Provenance & Evidence