Dimethyl Sulfoxide → (4-Vinylphenyl)acetonitrile

HRID 11973

Reaction equation

HRID 11973 reaction equation
[CH:1]([C:3]1[CH:10]=[CH:9][C:6]([CH2:7]Cl)=[CH:5][CH:4]=1)=[CH2:2].CS(C)=O.[C-:15]#[N:16].[K+]>O>[CH:1]([C:3]1[CH:10]=[CH:9][C:6]([CH2:7][C:15]#[N:16])=[CH:5][CH:4]=1)=[CH2:2]

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 9032Potassium CyanideHCID 74126p-Vinylbenzyl chloride

Product 1

HCID 3944539(4-Vinylphenyl)acetonitrile

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 22.2 g 4-vinyl benzylchloride (0.131 mol), 60 mL dimethylsulfoxide, and 12.8 g potassium cyanide (0.196 mol) was stirred at room temperature for 17 hours. The mixture was poured into 500 mL water and extracted several times with ethyl acetate. The combined organic layers were washed with brine and concentrated under vacuum. The crude red oil was purified by column chromatography on silica gel using 7/93 ethyl acetate/hexane to give 4-vinylbenzylcyanide, a yellow oil (18.03 g, 96%).

Workup

  1. extractionextracted several times with ethyl acetate
  2. washThe combined organic layers were washed with brine
  3. concentrationconcentrated under vacuum
  4. customThe crude red oil was purified by column chromatography on silica gel using 7/93 ethyl acetate/hexane

Sources & evidence

ORD record
ord-fedfeb7246d14800a6bb242376675b00
Source dataset
uspto-grants-2006_08
Patent number
US07098525B2

Linked notes

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