Water → 4-Tetradecyloxybenzyl alcohol

Participants

Reaction Conditions

Reaction Steps

To about 13.61 g of lithium aluminum hydride in about 200 ml of tetrahydrofuran was added, over about 1/2 hour, a solution of about 130 g of 4-tetradecyloxybenzoate in about 400 ml of tetrahydrofuran, in an ice bath with stirring and maintaining the temperature below about 40° C. After stirring about 2 hours the mixture was cooled to about 0° C., about 9 ml of water was added dropwise followed by the dropwise addition of about 18 ml of about 15% sodium hydroxide and about 30 ml of water. This mixture was filtered through celite, the solvent was removed and the residue recrystallized from ethanol, giving about 94.5 g of the desired title compound as a white solid, mp 75°-76° C.

Provenance & Evidence