Methanol → 3,7-Dimethyl-2-phenyl-octa-2,6-diene nitrile

HRID 513976

Reaction equation

HRID 513976 reaction equation
[CH3:1][C:2]([CH3:9])=[CH:3][CH2:4][CH2:5][C:6](=O)[CH3:7].[CH2:10]([C:17]#[N:18])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[OH-].[K+].CO>>[CH3:7][C:6]([CH2:5][CH2:4][CH:3]=[C:2]([CH3:9])[CH3:1])=[C:10]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:17]#[N:18]

Participants

5

Reactant 4

HCID 887MethanolHCID 8794PhenylacetonitrileHCID 98626-Methyl-5-hepten-2-oneHCID 14797Potassium Hydroxide

Product 1

HCID 675271983,7-Dimethyl-2-phenyl-octa-2,6-diene nitrileYield 24%

Procedure

To the mixture of 6-methyl-hept-5-en-2-one (90.86 g, 0.72 mol) and benzyl cyanide (46.8 g, 0.40 mol) is added dropwise a 4 N solution of KOH in MeOH (25.0 ml, 0.10 mol). The resulting suspension is heated to reflux during 4.5 h. Then methanol is removed by distillation and the residue is washed with 6 N aq. HCl-solution, then water, sat. aq. NaHCO3-solution and brine. The organic layer is dried over MgSO4, the solvent removed under reduced pressure and the residue distilled twice over a Widmer column to yield 3,7-Dimethyl-2-phenyl-octa-2,6-diene nitrile (21.5 g, 24%, (E/Z) mixture) as a colourless oil (b.p. 122DC/0.1 mbar).

Workup

  1. temperatureThe resulting suspension is heated
  2. temperatureto reflux during 4.5 h
  3. customThen methanol is removed by distillation
  4. washthe residue is washed with 6 N aq. HCl-solution
  5. dry with materialThe organic layer is dried over MgSO4
  6. customthe solvent removed under reduced pressure
  7. distillationthe residue distilled twice over a Widmer column

Sources & evidence

ORD record
ord-10934ee530284961993b77e722fe1d09
Source dataset
uspto-grants-2015_08
Patent number
US09102899B2

Linked notes

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