Water → (4-Vinylphenyl)acetonitrile

HRID 1884801Notes

Reaction equation

HRID 1884801 reaction equation
[C-:1]#[N:2].[Na+].O.Cl[CH2:6][C:7]1[CH:14]=[CH:13][C:10]([CH:11]=[CH2:12])=[CH:9][CH:8]=1>C(O)C>[C:1]([CH2:6][C:7]1[CH:14]=[CH:13][C:10]([CH:11]=[CH2:12])=[CH:9][CH:8]=1)#[N:2]

Participants

5

Reactant 3

HCID 962WaterHCID 8929Sodium Cyanide2×HCID 74126p-Vinylbenzyl chloride

Product 1

HCID 3944539(4-Vinylphenyl)acetonitrile

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
65 °C

Procedure

In a 500 μl 4-opening flask equipped with a stirring bar, 49.01 g of sodium cyanide was mixed with 70.07 g of water and 50.96 g of ethanol. Then, the temperature of the flask was elevated to 60° C. and the sodium cyanide was completely dissolved. To said solution, 87.50 g of 4-chloromethylstyrene was slowly added and it was reacted for 3 hours while stirring and maintaining the reaction temperature within 60-70° C. When the reaction terminated, said solution was cooled to 40° C., and 100 g of diethylether was added and the diethylether layer was separated. The separated organic layer was extracted with 300 g of water three times, and the water layer was extracted with 50 g of diethylether and was combined with said organic layer. The separated obtained organic layer was dried with magnesium sulfate for one day, and then the organic solvent was removed using an evaporator to obtain the product 4-cyanomethylstyrene. The yield of the product was 80%, and the product was a deep purple color.

Workup

  1. customIn a 500 μl 4-opening flask equipped with a stirring bar
  2. customwas elevated to 60° C.
  3. additionwas slowly added
  4. customit was reacted for 3 hours
  5. customWhen the reaction terminated
  6. temperaturewas cooled to 40° C.
  7. addition100 g of diethylether was added
  8. customthe diethylether layer was separated
  9. extractionThe separated organic layer was extracted with 300 g of water three times
  10. extractionthe water layer was extracted with 50 g of diethylether
  11. customThe separated obtained organic layer
  12. dry with materialwas dried with magnesium sulfate for one day
  13. customthe organic solvent was removed
  14. customan evaporator

Sources & evidence

ORD record
ord-6568bc16f1594a6dad8409554cbaeed1
Source dataset
uspto-grants-2004_07
Patent number
US06767687B1

Reaction notes

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