Dimethyl Sulfoxide → 2-(Benzyloxy)-3-(hexadecyloxy)propan-1-ol

Participants

Reaction Conditions

Reaction Steps

A stirred solution of 9.36 g of oxalyl chloride in 130 ml of methylene chloride, under an argon atmosphere was cooled to -70° C. To this was added dropwise 11.53 g of dried dimethyl sulfoxide at a rate to maintain the temperature at -65° to -70° C. After stirring 5 minutes a solution of 10 g of 3-(hexadecyloxy)-2-(phenylmethoxy)-1-butanol in 60 ml of methylene chloride was added dropwise at a fast rate. The pasty mixture was allowed to warm to -10° C. over 20 minutes providing a solution. This solution was recooled to -50° C. and 16.17 g of triethylamine was added dropwise. The reaction mixture was allowed to warm to room temperature and was then poured into 100 ml of water. The organic phase was separated, washed successively with 0.5N hydrochloric acid, saturated aqueous sodium bicarbonate and brine, dried and the solvents removed giving an oil. This oil was dissolved in petroleum ether, washed with water and taken to dryness, giving 10 g of the desired compound as a yellow oil.

Provenance & Evidence