Oxygen → Ethyl sorbate

Participants

Reaction Steps

A mixture of 10 mmol of ethyl acrylate, 100 mmol of n-propyl alcohol, 1 mmol of N-hydroxyphthalimide, 0.01 mmol of cobalt(II) acetate, 0.1 mmol of acetylacetonatocobalt(III), and 54 mmol of acetonitrile was stirred at 50° C. in an oxygen atmosphere (1 atm) for 8 hours. A reaction mixture was concentrated, and the concentrate was subjected to column chromatography on a silica gel to yield ethyl 2,4-dihydroxyhexanoate, γ-ethyl-α-hydroxy-γ-butyrolactone, and ethyl sorbate in yields of 14%, 40%, and 2%, respectively. The conversion rate from ethyl acrylate was 72%.

Provenance & Evidence