Oxalic Acid → 16-(m-Methylphenoxy)-hexadeca-5,8,11,14-tetraynoicacid

Participants

Reaction Steps

185 mg of 16-(m-methylphenoxy)hexadeca-5,8,11,14-tetraynoic acid methyl ester was treated with 21 ml of a pH 6.7 buffer solution (prepared as described in Example 1) and 1.98 g of Sigma Lipase, Type VII, from Candidacylindracea and sonicated for 30 minutes at room temperature. The reaction mixture was then transferred to a separatory funnel with ethyl acetate (200 ml) and acidified to pH ~3 with a saturated solution of oxalic acid. The organic layer was separated, dried over sodium sulfate and the solvent removed in vacuo. The residue was purified by thin layer chromatography in silica gel with a Chromatatron (model 7924, Harrison Research, Palo Alto, CA) using hexane:ethyl acetate:acetic acid (70:30:1) as the eluant, yielding 16-(m-methylphenoxy)-hexadeca-5,8,11,14-tetraynoicacid, as an oil. The product was stored in dry ice.

Provenance & Evidence