Water → 15-Hydroxypentadecanoic acid

Participants

Reaction Steps

After triphenylphosphine (366 mg, 1.39 mmol) and THF (135 mL) were added to a 300 mL flask, azodicarboxylic acid bis(2-methoxyethyl) ester (367 mg, 1.39 mmol) dissolved in THF (30 mL) was added dropwise thereto at 20° C. Subsequently, 15-hydroxypentadecanoic acid (300 mg, 1.16 mmol) dissolved in THF (60 mL) was added dropwise thereto at 20° C., and the reaction was allowed to proceed for 12.5 hours. Water (0.5 mL) was added, and concentration was carried out. Then, water (15 ml) was added to the solution, and extraction was carried out using diethyl ether (15 ml, ×2). Then, the organic layer was washed with water (15 mL) and saturated salt water (15 ml), and dehumidified with anhydrous magnesium sulfate. Subsequently, a crude product obtained by concentration was purified by column chromatography (silica gel, 5% ethyl acetate-hexane solution) to give 15-pentadecanolactone as a white solid substance (86 mg, yield: 31%/15-hydroxypentadecanoic acid).

Provenance & Evidence