Oxalic Acid → HCID 14578982, compound

Participants

Reaction Steps

540 mg of 16-phenoxyhexadeca-5,8,11,14-tetraynoic acid methyl ester weretreated with 64 ml of a pH 6.7 buffer solution (disodium hydrogen phosphate-potassium dihydrogen phosphate) obtained as described in Example1. The emulsion was vigorously stirred and 6.17 g of Sigma Lipase, Type VII, from Candida cylindracea was added, stirring for 8 hours at room temperature. The reaction mixture was then transferred to a separatory funnel with ethyl acetate (100 ml), and then acidified with saturated solution of oxalic acid. The organic phase was separated, dried over sodium sulfate and the solvent removed under vacuo. The residue was purified by TLC on silica gel with a Chromatotron using hexane:ethyl acetate:acetic acid (60:40:1) as the eluant. The crude product was crystallized from benzene-hexane, to yield 16-phenoxyhexadeca-5,8,11,14-tetraynoic acid. M.P. 74°-76° C. (dec.). The product was stored in dry ice.

Provenance & Evidence