Icosanal (1 g, 3.37 millimole) and methyl 2-bromohexadecanoate (977.8 mg, 2.80 millimole) were dissolved in the same mixed solvent (30 ml). The obtained solution (4 ml) was added dropwise to the reaction vessel containing zinc activated by trimethylchlorosilane as described above, and the mixture was stirred at 85° C. for 1 hour. The progress of reaction was confirmed through thin layer chromatography, and the rest of the solution (26 ml) was gradually added under the same conditions and the mixture was stirred for 8 hours. After cooling the reaction mixture with ice, 20% sulfuric acid (50 ml) was added thereto, and the, mixture,, was stirred for 15 minutes. Then the mixture was extracted twice with benzene, and the organic phase was washed twice with 10% sulfuric acid, and successively washed once with saturated aqueous sodium bicarbonate solution, once with 10% sulfuric acid, then twice with water, and dried over anhydrous sodium sulfate. The solvent was distilled off from the organic phase, and the obtained residue was dissolved in a developing solvent (n-hexane:ether=8:2) and fractionated through silicagel column chromatography (n-hexane:ether=8:2). The fourth and fifth fractions were pooled and the solvent was distilled off to give methyl 3-hydroxy-2-n-tetradecyl-docosanoate (III) (812.8 mg, yield 51%) in the form of white crystals.
