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

Participants

Reaction Conditions

Reaction Steps

A mixture of sodium hypochlorite (100 ml, 13% w/v) and saturated sodium bicarbonate (25 ml) was added in one charge to a stirred solution of 1,3-dibenzyloxy-2-propanol (10 g) and 2,2,6,6-tetramethyl-1-piperidinyloxy free radical, (TEMPO) (0.3 g) in toluene (40 ml). The biphasic mixture was stirred at 20-25° C. for 15 minutes when HPLC analysis showed reaction to be complete. The reaction mixture was stirred for a total of 25 minutes at 23° C. The reaction mixture was separated and the organic extract was washed with 5% w/v sodium thiosulfate solution (40 ml) and separated. The organic extract was washed with 1% w/v sodium chloride solution (2×25 ml). The organic extract was then concentrated in vacuo to give an oil which crystallised on standing to give 8.8 g of 1,3-dibenzyloxy-2-propanone in 88.7% yield. The NMR spectrum of the product was concordant with a reference sample.

Provenance & Evidence