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

Participants

Reaction Conditions

Reaction Steps

A solution of 1,3-dibenzyloxy-2-propanol (500 g, 1.84 mol 1.0 eq.), TEMPO (5.5 g, 0.034 mol) in dichloromethane (1.25 L) was placed in a 10 L flange flask fitted with overhead stirrer. A solution of potassium bromide (48 g, 0.40 mol) in water (185 ml) was added and the reaction stirred and cooled to −10° C. A 14% aqueous NaOCl solution was diluted to 1M (2145 g diluted to 4050 ml). The pH of this solution was then adjusted to 9.5 by dissolving NaHCO3 (80 g) immediately before use. This NaOCl solution was added over 1 hour, keeping the temperature of the reaction mixture between 10-15° C. The mixture was the stirred for 60 minutes. The orange coloured organic phase was separated and the aqueous layer was extracted with dichloromethane (5.0 L, 2.0 L). The combined organics were washed with 10% aq. HCl (10.75 L) containing potassium iodide (143 g), 10% aq. Na2S2O5 (5.0 L) and water (5.0 L). The organics were dried over MgSO4 and concentrated under reduced pressure to give the crude title compound (893 g, 90%). This compound was taken through to the next step without further purification.

Provenance & Evidence