1,3-Propanediol → 1,3-Di-(z-15-tetracosenoyloxy)propane

Participants

Reaction Conditions

Reaction Steps

z-15-Tetracosenoic acid (available from Sigma Chemicals), (0.286 mol, 104.7 g), propane-1,3-diol (0.136, 10.3 g) and hypophosphorous acid (0.4 g) was heated with stirring to 160° C. under nitrogen. After 6 h, TLC (80:18:2 petroleum ether-ethyl ether-acetic acid) indicated that the reaction had gone to completion (Rf: 0.63). The mixture was cooled down to room temperature and petroleum ether (1500 mL) was added. The resulting solution was washed with saturated sodium bicarbonate (3×150 mL) and saturated sodium chloride (3×150 mL). It was then dried over anhydrous sodium sulphate and concentrated to dryness. Residual mono-ester and fatty acid were removed by distillation in vacuo (230° C., 10−2 mbar). The resulting oil was dissolved into petroleum ether to make up a 33% solution and was passed down a silica column. Hexane was finally removed to yield 1,3-di-(z-15-tetracosenoyloxy)propane as a colourless oil.

Provenance & Evidence