Methyl Ethyl Ketone → HCID 67526854, compound

HRID 513974Notes

Reaction equation

HRID 513974 reaction equation
[CH3:1][C:2](=O)[CH2:3][CH3:4].[CH2:6]([C:13]#[N:14])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C[O-].[Na+]>>[CH3:1][C:2]([CH2:3][CH3:4])=[C:6]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[C:13]#[N:14]

Participants

4

Reactant 3

HCID 6569Methyl Ethyl KetoneHCID 8794PhenylacetonitrileHCID 10942334Sodium Methoxide

Product 1

HCID 67526854HCID 67526854, compoundYield 22.2%

Conditions

Temperature
60 °C

Procedure

Butanone (45.0 g, 0.63 mol) is added to the mixture of benzyl cyanide (58.5 g, 0.50 mol) and sodium methoxide (30% in MeOH, 34.3 ml, 0.185 mol) and the resulting suspension is heated to 60° C. (oilbath) and stirred for 6 h at this temperature. The product is extracted with cyclohexane, washed with dilute NaHCO3-solution and brine. The organic layer is dried over MgSO4, the solvent removed under reduced pressure and the residue distilled over a short-path apparatus at 0.05 mbar. The fraction distilling at 90° C. is collected (45 g) and subjected to a fine distillation over a Widmer-column to yield olfactorily pure 3-methyl-2-phenyl-pent-2-ene nitrile (19 g, 22%) as a colourless oil (b.p. 102° C./0.05 mbar). (E/Z) ratio about 55:45.

Workup

  1. extractionThe product is extracted with cyclohexane
  2. washwashed with dilute NaHCO3-solution and brine
  3. dry with materialThe organic layer is dried over MgSO4
  4. customthe solvent removed under reduced pressure
  5. distillationthe residue distilled over a short-path apparatus at 0.05 mbar
  6. distillationThe fraction distilling at 90° C.
  7. customis collected (45 g)
  8. distillationsubjected to a fine distillation over a Widmer-column

Sources & evidence

ORD record
ord-c4abc253e19245489e8e054e33ea3bda
Source dataset
uspto-grants-2015_08
Patent number
US09102899B2

Reaction notes

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