Water → gamma-Linolenyl alcohol

Participants

Reaction Steps

To a suspension of lithium aluminium hydride (50 g) in diethyl ether (1400 ml) under nitrogen was added dropwise with stirring a solution of z,z,z-octadeca-6,9,12-trienoic acid (97%, 200 g) at such a rate that a steady reflux occurred. The mixture was heated under reflux for 4 hours. After cooling to 0°-5° C., water (200 ml) was added cautiously to break down the complex, still maintaining a blanket of nitrogen. To the resulting slurry was added a 10% aqueous solution of sulphuric acid (1500 ml) and a two phase solution occurred. The aqueous layer was separated and the organic layer was washed with water (1000 ml), saturated aqueous sodium bicarbonate (2×1000 ml) and water (2×500 ml). The ether layer was dried (Na2SO4) and evaporated in vacuo to give a yellow oil. Distillation (148°-150° C./0.06 mmHg) gave z,z,z,-octadeca-6,9,12-trienol (179 g, 94% ) as a colourless oil.

Provenance & Evidence