Water → 1-O-octadecyl-sn-glycerol

Participants

Reaction Steps

20 ml of (R)-(−)-2,2-dimethyl-1,3-dioxolane-4-methanol, 27 grams of powdered potassium hydroxide and 59 grams of 1-bromooctadecane were stirred in 250 ml benzene and refluxed for 6 hours, while removing the water formed by azeotropic distillation. The volume of the solvent was gradually reduced to about 200 ml. The reaction mixture was then cooled to room temperature and stirred at this temperature overnight. 200 ml water was added, the reaction mixture extracted twice with 200 ml diethyl ether, the combined organic phase was washed with 200 ml water, and the solvent was then removed under reduced pressure. The obtained residue was dissolved in 100 ml of a mixture of 90:10:5 (v/v) methanol:water:concentrated hydrochloric acid, and the resulting solution was refluxed for 1 hour, followed by cooling to room temperature and addition of 200 ml water. The product was extracted twice with 200 ml chloroform, washed consecutively with 200 ml water, 200 ml of a saturated aqueous solution of sodium carbonate, and again with 200 ml water. The solvent was then removed under reduced pressure, and the crude product was crystallized from 500 ml hexane to give 39.5 grams of pure (S)-1-octadecyl-glycerol, which was dried in a desiccator under reduced pressure with phosphorus oxide.

Provenance & Evidence