Acetyl bromide → 9,12-Octadecadienoic acid (9Z,12Z)-, 1-((acetyloxy)methyl)-2-((1-oxohexadecyl)oxy)ethyl ester

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Reaction Steps

Acetylbromide (123 g) was added into heptane solution of 1-palmitoyl-2-linoleoyl-3-t-butyl-dimethylsilyl-glycerol, which was obtained in Example 4, and the reaction mixture was stirred for 12 hours at room temperature. Heptane (400 ml) was added into the reaction mixture, and the cooling purified water (400 ml) was dropwisely added thereto for extracting the organic layer. The separated organic layer was washed with a solution of saturated sodium bicarbonate (100 ml) and purified water (400 ml), and then the washed organic layer was dehydrated with anhydrous MgSO4, and filtered. 1-palmitoyl-2-linoleoyl-3-acetyl-glycerol (178 g) was obtained with a silica gel (Si-60, 230-400 mesh) column chromatography(heptane:ethyl acetate=36:1 by volume) (theoretical amounts: 63.5 g, yield: 28.0%).

Provenance & Evidence