Diethyl Ether → 2,2,2-Trichloroethyl-2-[(z,z,z) octadeca-6,9,12-trienoyl]benzoate

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--To a solution of 2,2,2-trichloroethyl salicylate (104 g) in dry pyridine (500 ml) at 0°-5° C. and under nitrogen was added (z,z,z)octadeca-6,9,12-trienoyl chloride (137.5 g) dropwise over a period of one hour. The reaction mixture was allowed to stir for twenty hours at room temperature and then the pyridine was removed in vacuo (25° C./0.5 mmHg). The residue was dissolved in diethyl ether (2000 ml) and water (1000 ml) and the resulting two phase system was shaken and acidified slowly to pH1 by addition of 2M hydrochloric acid. The diethyl ether layer was separated and washed with water (4×1000 ml), adding sodium chloride to break any emulsion that formed. After drying the organic layer (Na2SO4), the solvent was removed in vacuo to give an orange/brown oil. This was subjected to MPLC (Column size: 15 cm dia.×40 cm, Column packing: Matrex silica, pore size 60A, particle size 35-70 μm, Solvent: initially hexane, then 15% diethyl ether in hexane, Fraction size: 1000 ml). The requisite fractions were evaporated in vacuo to give 2,2,2-trichloroethyl-2-[(z,z,z) octadeca-6,9,12-trienoyl]benzoate. (189 g, 93% yield) as a pale yellow oil.

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