Acetone → 3-Methyl-2-p-tolyl-but-2-ene nitrile

HRID 513975Notes

Reaction equation

HRID 513975 reaction equation
[C:1]1([CH3:10])[CH:6]=[CH:5][C:4]([CH2:7][C:8]#[N:9])=[CH:3][CH:2]=1.[OH-].[K+].[CH3:13][C:14]([CH3:16])=O>CO>[CH3:13][C:14]([CH3:16])=[C:7]([C:4]1[CH:5]=[CH:6][C:1]([CH3:10])=[CH:2][CH:3]=1)[C:8]#[N:9]

Participants

5

Reactant 3

HCID 180AcetoneHCID 14797Potassium HydroxideHCID 76280p-Tolylacetonitrile

Product 1

HCID 112752763-Methyl-2-p-tolyl-but-2-ene nitrileYield 15%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
65 °C

Procedure

p-Tolylacetonitrile (18.5 g, 0.14 mol) is dissolved in a mixture of acetone (50 ml) and methanol (6.7 ml) and KOH (3.33 g, 0.05 mol) is added. The resulting mixture is heated to 65° C. (oilbath) and stirred for 3 h. The volatiles are removed in a rotary evaporator, the residue is dissolved in toluene and washed 3 times with half saturated aq. NaCl-solution. The organic layer is dried over MgSO4, the solvent removed under reduced pressure and the residue distilled over a short-path apparatus at 0.06 mbar. The fraction distilling at 77° C. is collected (11 g) and subjected to a fine distillation over a Widmer-column to yield 3.54 g (15%) of 3-methyl-2-p-tolyl-but-2-ene nitrile as colourless oil (b.p. 90-95° C./0.05 mbar).

Workup

  1. additionis added
  2. customThe volatiles are removed in a rotary evaporator
  3. dissolutionthe residue is dissolved in toluene
  4. washwashed 3 times with half saturated aq. NaCl-solution
  5. dry with materialThe organic layer is dried over MgSO4
  6. customthe solvent removed under reduced pressure
  7. distillationthe residue distilled over a short-path apparatus at 0.06 mbar
  8. distillationThe fraction distilling at 77° C.
  9. customis collected (11 g)
  10. distillationsubjected to a fine distillation over a Widmer-column

Sources & evidence

ORD record
ord-0090f8012fde4194bf0180584390d306
Source dataset
uspto-grants-2015_08
Patent number
US09102899B2

Reaction notes

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