Acrylonitrile → Methyl Undecenoate Acrylonitrile

Participants

Reaction Steps

100 mg of methyl 10-undecenoate (0.5 mmol), 53 mg of acrylonitrile (1 mmol) and 8 ml of toluene distilled over sodium-benzophenone are placed in a 50 ml second-generation Hoveyda-Grubbs catalyst dissolved in 2 ml of toluene is added, using a syringe and a syringe press, over a period of 2 hours 40 minutes, under nitrogen and with magnetic stirring. At the end of the addition, the mixture is left to react for 1 hour at 80° C. The reaction mixture is analyzed by gas chromatography (dodecane standard). The conversion of the methyl 10-undecenoate is 94%. The selectivity toward methyl 11-cyano-10-undecenoate (cis+trans mixture) is 100%. The TON is 940.

Provenance & Evidence