Phosphinic Acid → 1-(z,z,z-6,9,12-Octadecatrienoyloxy)-3-(z-15-tetracosenoyloxy)propane

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A mixture of 1-hydroxy-3-(z-15-tetracosenoyloxy)propane, prepared according to Description 3, (0.045 mol, 19.0 g), z,z,z-6,9,12-octadecatrienoic acid (0.054 mol, 15.0 g) and hypophosphorous acid (0.4 g) was heated with stirring to 160° C. under nitrogen. After 5 h, TLC (80:18:2 petroleum ether-ethyl ether-acetic acid) indicated that most of the mono-ester had reacted (Rf: 0.60). The mixture was cooled down to room temperature and petroleum ether (800 mL) was added. The resulting solution was washed with saturated sodium bicarbonate (3×80 mL) and saturated sodium chloride (3×80 mL). It was then dried over anhydrous sodium sulphate, concentrated and purified by flash chromatography on silica gel (19:1 petroleum ether-ethyl ether) to yield 1-(z,z,z-6,9,12-octadecatrienoyloxy)-3-(z-15-tetracosenoyloxy)propane as a pale yellow oil.

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