ethyl (Z)-8-methylnon-6-enoate

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 223.12 g (1 mol) of ethyl 6-bromohexanoate and 275.4 g (1.05 mol) of triphenyl phosphine were refluxed for 36 hours in 1.5 l of acetonitrile. After the reaction was terminated, 500 ml of acetonitrile was distilled off, then the reaction mixture was dried. Into the dried mixture, 72.11 g (1 mol) of isobutyl aldehyde was added and stirred. Controlling the reaction temperature in the range of 25°-35° C., 40 g (1 mol) of oily (60%) sodium hydride was carefully added. Then, the reaction mixture was stirred over night at room temperature. After the reaction was ended, 500 g of water was added into the reaction mixture, the oil layer was then separated and the water layer was extracted twice with 300 ml of hexane. The organic layers were combined and washed with 300 ml of water, solvent was removed in vacuum under reduced pressure, and then distilled under 2 mm Hg to obtain 122.8 g of ethyl 8-methyl-6-nonenoate (Yield: 62% based upon the starting material). After the reaction was terminated 500 ml of acetonitrile was distilled off the reaction mixture was dried was carefully added Then, the reaction mixture was stirred over night at room temperature the oil layer was then separated the water layer was extracted twice with 300 ml of hexane washed with 300 ml of water, solvent was removed in vacuum under reduced pressure distilled under 2 mm Hg