HCID 5363514, compound → HCID 54300712, compound

Participants

Reaction Steps

To prepare (E,E)-10,12-tetradecadien-1-ol acetate (I), the tetradecadiene (D) (5.6 g) in 200 ml methanol containing eight drops concentrated HCl was refluxed for 15 minutes. After the solution was cooled, 400 ml of water was added, and the mixture was extracted three times with hexane. The hexane extract was dried over sodium sulfate, and the hexane was removed with a rotary evaporator leaving 3 g crude 10,12-tetradecadienol, which was purified by silica gel liquid chromatography. Unwanted side products were eluted with 10% ether/hexane, and the alcohol was eluted with 50% ether/hexane, giving 2.4 g (66% yield based on the dodecenenitrile (B)).

Provenance & Evidence