Oxalic Acid → 16-(p-Methylthiophenoxy)hexadeca-5,8,11,14-tetraynoic acid

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Reaction Steps

1.7 g of 16-(p-methylthiophenoxy)hexadeca-5,8,11,14-tetraynoic acid ethyl ester was mixed with 168 ml of the pH 6.7 buffer solution prepared in accordance with Example 1. The mixture was vigorously stirred and 16.24g of Sigma Lipase, Type VII, from Candida cylindracea were added, stirring was continued for 18 hours at room temperature; the reaction mixture was then transferred to a separatory funnel with 200 ml ethyl acetate and acidified with saturated solution of oxalic acid. The organic layer was separated and the aqueous layer extracted with ethyl acetate. The combinedorganic extract was dried over sodium sulfate and the solvent removed undervacuo. The residue was purified by TLC on silica gel with a Chromatotron using hexane-ethyl acetate (60:40) as the eluant, to yield 16-(p-methylthiophenoxy)hexadeca-5,8,11,14-tetraynoic acid, which was recrystallized from methylene chloride-hexane. M.P. 87°-88° C. (dec).

Provenance & Evidence