Benzyl Chloride → 3-(Benzyloxy)-1,2-propanediol

Participants

Reaction Conditions

Reaction Steps

The 50 ml of a 50% (w/v) sodium hydroxide solution are added 33 g (0.25 mole) of isopropylideneglycerol, 30.25 ml (0.25 mole) of benzyl chloride and 1.38 g (4 millimoles) of benzoyl chloride and 1.38 g (4 millimoles) of benzyltri-n-butylammonium. The mixture is stirred at 100° C. for 5 hours, then cooled to room temperature, diluted with 50 ml of water and extracted with ether. The extract is washed with water and then the solvent is distilled off under reduced pressure. To the residue is added 70 ml of 15% (w/v) sulfuric acid, and the mixture is stirred at 100° C. for 2.5 hours. After cooling, the unreacted material is removed by extraction with petroleum ether, the aqueous layer is neutralized and then extracted with ethyl acetate, and the extract is washed with a saturated sodium chloride solution and dried over anhydrous sodium sulfate. The solvent is then distilled off under reduced pressure to give about 21 g of a yellow oil.

Provenance & Evidence