Acrylonitrile → Methyl Undecenoate Acrylonitrile

HRID 239234

Reaction equation

HRID 239234 reaction equation
[C:1]([O:13][CH3:14])(=[O:12])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH:10]=[CH2:11].[C:15](#[N:18])[CH:16]=[CH2:17].[Na].C(C1C=CC=CC=1)(=O)C1C=CC=CC=1.CCCCCCCCCCCC.C(C=CCCCCCCCCC(OC)=O)#N>CC1C=C(C)C(N2C(=[Ru](Cl)(Cl)=CC3C=CC=CC=3OC(C)C)N(C3C(C)=CC(C)=CC=3C)CC2)=C(C)C=1.C1(C)C=CC=CC=1>[C:1]([O:13][CH3:14])(=[O:12])[CH:2]=[CH:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11].[C:15](#[N:18])[CH:16]=[CH2:17]

Participants

8

Reactant 5

HCID 7855AcrylonitrileHCID 8138Methyl 10-undecenoate2×HCID 8182DodecaneHCID 66591377Sodium benzophenoneHCID 85444428Methyl 11-cyano-10-undecenoate

Product 1

HCID 86643178Methyl Undecenoate Acrylonitrile

Reagents, catalysts & solvents 2

HCID 11763533(1,3-Bis(2,4,6-trimethylphenyl)imidazolidin-2-ylidene)(dichloro)((2-((propan-2-yl)oxy)phenyl)methylidene)rutheniumCatalystHCID 1140TolueneSolvent2×

Procedure

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.

Workup

  1. additionis added
  2. additionAt the end of the addition
  3. waitthe mixture is left
  4. customto react for 1 hour at 80° C

Sources & evidence

ORD record
ord-a9d9380a26bd4c04a645aa8280f1f09b
Source dataset
uspto-grants-2014_02
Patent number
US08642792B2

Linked notes

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