Sodium Cyanide → 2-(p-Prenylphenyl)propionitrile

HRID 1413832Notes

Reaction equation

HRID 1413832 reaction equation
Cl[CH:2]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH:11]=[C:12]([CH3:14])[CH3:13])=[CH:6][CH:5]=1)[CH3:3].[C-:15]#[N:16].[Na+]>>[CH2:10]([C:7]1[CH:8]=[CH:9][C:4]([CH:2]([CH3:3])[C:15]#[N:16])=[CH:5][CH:6]=1)[CH:11]=[C:12]([CH3:14])[CH3:13]

Participants

3

Reactant 2

HCID 8929Sodium CyanideHCID 132919731-Chloro-1-(p-prenylphenyl)ethane

Product 1

HCID 135850232-(p-Prenylphenyl)propionitrileYield 81.8%

Procedure

A mixture of 21.0 g of 1-chloro-1-(p-prenylphenyl)ethane, 11.3 g of sodium cyanide and 140 ml of dimethylsufoxide was stirred at 60°-65° C. for 7 hours. After cooling, 400 g of ice-water was added and the resulting solution was extracted with n-hexane. The extract was washed with water, concentrated and distilled to give 16.4 g of 2-(p-prenylphenyl)propionitrile, b.p. 108-110 °C/0.28 mmHg.

Workup

  1. temperatureAfter cooling
  2. extractionthe resulting solution was extracted with n-hexane
  3. washThe extract was washed with water
  4. concentrationconcentrated
  5. distillationdistilled

Sources & evidence

ORD record
ord-74133b1a0cac4a999e37fac10338a28c
Source dataset
uspto-grants-1981_02
Patent number
US04251543

Reaction notes

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