Methanol → 16-Hydroxyhexadecanoic acid

Participants

Reaction Conditions

Reaction Steps

A compound of General formula 4 (n=10) (2.72 g, 10 mmole) was mixed with 2.0 g of ground sodium hydroxide, 16 ml of diethylene glycol, 1.3 ml of 85% hydrated hydrazine, and 0.6 ml of methanol, and stirred at 110° C. for 30 min. The mixture was heated up to 195-200° C. and stirred for 15 hours. Distillable components were completely distilled off to ensure its removal out of the system. The residue was cooled, acidified and subjected to extraction with chloroform. The chloroform layer was washed with water, and dried over anhydrous magnesium sulfate, and the solvent was distilled off to provide a crystalline material. It was recrystallized from benzene to produce 2.1 g of 15-hydroxypentadecanoic acid 2 (n=10). The yield was 81%. The product had a melting point of 84-86° C. The structure of 15-hydroxypentadecanoic acid was confirmed from IR and NMR spectral observation.

Provenance & Evidence