Acetonitrile → 3-(4-Methylphenyl)-3-phenylprop-2-enenitrile

HRID 742325Notes

Reaction equation

HRID 742325 reaction equation
[OH-].[K+].[CH3:3][C:4]1[CH:17]=[CH:16][C:7]([C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=O)=[CH:6][CH:5]=1.[C:18](#[N:20])[CH3:19]>>[CH3:3][C:4]1[CH:17]=[CH:16][C:7]([C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:19][C:18]#[N:20])=[CH:6][CH:5]=1

Participants

4

Reactant 3

HCID 6342Acetonitrile2×HCID 86524-MethylbenzophenoneHCID 14797Potassium Hydroxide

Product 1

HCID 543823533-(4-Methylphenyl)-3-phenylprop-2-enenitrileYield 78%

Procedure

To a solution of 6.5 g (0.114 mol) of KOH in 70 mL of acetonitrile was added dropwise under argon a solution of 4-methylbenzophenone (22.5 g, 0.114 mol) in acetonitrile (45 mL). After the addition was complete, the reaction mixture was heated at reflux overnight. It was then allowed to cool, poured into ice and extracted with dichloromethane. The organic phase was dried and the solvent was removed to afford 30 g of a crude product that was chromatographed on silica gel (hexane-ethyl acetate mixtures of increasing polarity) to give 19.5 g of the desired product (yield: 78%).

Workup

  1. additionAfter the addition
  2. temperaturethe reaction mixture was heated
  3. temperatureat reflux overnight
  4. temperatureto cool
  5. additionpoured into ice
  6. extractionextracted with dichloromethane
  7. customThe organic phase was dried
  8. customthe solvent was removed
  9. customto afford 30 g of a crude product that
  10. customwas chromatographed on silica gel (hexane-ethyl acetate mixtures of increasing polarity)

Sources & evidence

ORD record
ord-af2b47b2332b461dba3d501c734f6b35
Source dataset
uspto-grants-1996_09
Patent number
US05554624

Reaction notes

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