Sodium Cyanide → 2-Phenylbut-3-enenitrile

HRID 1742040Notes

Reaction equation

HRID 1742040 reaction equation
[CH:1]([CH:3](Cl)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=[CH2:2].[C-:11]#[N:12].[Na+]>CO.O>[CH:1]([CH:3]([C:11]#[N:12])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=[CH2:2]

Participants

4

Reactant 2

HCID 8929Sodium CyanideHCID 11768772Benzene, 1-(chloromethyl)-3(or 4)-ethenyl-

Product 1

HCID 147675092-Phenylbut-3-enenitrileYield 71%

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

12.2 g of commercially available vinylbenzyl chloride (a mixture of 60% of a meta-isomer and 40% of a para-isomer) were reacted with 5 g of NaCN in a mixed solvent of methanol/water=12.2 g/5 g at 64° C. for 12 hours. A reaction product solution was filtered, and the solvent was then distilled off, followed by distillation under reduced pressure, thereby obtaining 8.1 g of vinylbenzyl cyanide (yield 71%).

Workup

  1. filtrationA reaction product solution was filtered
  2. distillationthe solvent was then distilled off
  3. distillationfollowed by distillation under reduced pressure

Sources & evidence

ORD record
ord-a61aa2b44e454a1e831b5e9f53cd3be7
Source dataset
uspto-grants-1994_08
Patent number
US05336725

Reaction notes

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