Dimethyl Sulfoxide → 1,3-Bis(benzyloxy)propan-2-one

Participants

Reaction Steps

To a dichloromethane (200 ml) solution of 1,3 dibenzyloxy-2-propanol (52 g, 191 mmol), triethylamine (130 ml, 933 mmol), and dimethylsulfoxide (65 ml, 916 mmol), sulfur trioxide pyridine complex (131 g, 823 mmol) was added at 0° C. and stirred at 0° C. to room temperature for 2 hours. To the mixture, water and ethyl acetate were added. The organic layer was washed with 2N hydrochloric acid, water and an aqueous saline solution, dried over anhydrous sodium sulfate, and concentrated. As a result, the title compound (52.01 g, quantitative yield) was obtained as a brown oil.

Provenance & Evidence