Water → 3-Benzyl-1,2-dihexadecylglycerol

Participants

Reaction Steps

To a refluxing mixture of benzylglycerol (50 g, 0.27 mol) and KOH (40 g, 0.76 mol), which had been freshly powdered in an electric milling device, in toluene (500 mL) was added 1-bromohexadecane (252 g, 9.76 mol) over a period of one hour. The mixture was refluxed overnight, with Dean-Stark removal of water of reaction. The slurry was stripped of toluene on a rotary evaporator, then the residue was slurried in CHCl3 and washed with water. The organic phase was dried (MgSO4) and stripped. Unreacted starting material was removed by Kugelrohr distillation (150°, 1 mm Hg). The pot residue was a yellow solid of sufficient purity for use in the next step.

Provenance & Evidence