4-Nitrophenol → Hexadec-2-enoic acid

Participants

Reaction Steps

To a solution of 3-hydroxyhexadecanoic acid (2 g) in pyridine was added acetic anhydride at 0° C., and the mixture was stirred for 4 hours. The reaction mixture was distributed into chloroform-water, and the chloroform layer was concentrated. The residue obtained was dissolved in N,N-dimethylformamide (DMF). Para-nitrophenol (1.02 g) and N,N'-dicyclohexylcarbodiimide (1.51 g) were added to the solution, and the mixture was stirred for 12 hours. The reaction mixture was filtered and concentrated, and the residue was subjected to chromatography on a silica gel column with eluent systems of n-hexane-ethyl acetate (from 100:1 to 50:1) to give an active ester of 2-hexadecenoic acid (0.92 g) and an active ester of 3-acetoxyhexadecanoic acid (1.01 g).

Provenance & Evidence