Oxalic Acid → HCID 178526186, compound

Participants

Reaction Steps

A mixture of 1.7 g of 16-phenylthiohexadeca-5,8,11,14-tetraynoic acid ethyl ester, 184 ml of the pH 6.7 buffer solution of disodium hydrogen phosphate/potassium dihydrogen phosphate, prepared as in Example 1 and 17.5 g of Sigma Lipase, Type VII, from Candida cylindracea was sonicated for 5 hours at room temperature. The reaction mixture was then transferredto a separatory funnel with ethyl acetate (200 ml) and acidified with saturated solution of oxalic acid. The organic phase was separated and combined with ethyl acetate extracts of the aqueous phase. The ethyl acetate was dried over sodium sulfate and removed under vacuo. The residuewas purified by TLC on silica gel using a Chromatotron using hexane:ethyl acetate:acetic acid (60:40:1) as the eluant. The crude product was crystallized from methylene chloride-hexane, to yield 16-phenylthiohexadeca-5,8,11,14-tetraynoic acid. M.P. 69°-71° C. (dec), which was stored in dry ice.

Provenance & Evidence