Water → (4-Vinylphenyl)acetonitrile

HRID 351962

Reaction equation

HRID 351962 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. customit was reacted for 3 hours
  4. customWhen the reaction terminated
  5. temperaturewas cooled to 40° C.
  6. addition100 g of diethylether was added
  7. customthe diethylether layer was separated
  8. extractionThe separated organic layer was extracted with 300 g of water three times
  9. extractionthe water layer was extracted with 50 g of diethylether
  10. customThe separated obtained organic layer
  11. dry with materialwas dried with magnesium sulfate for one day
  12. customthe organic solvent was removed
  13. customan evaporator

Sources & evidence

ORD record
ord-a8346eeaec8b442fa32c0a8747ac8cc9
Source dataset
uspto-grants-2004_06
Patent number
US06743881B2

Linked notes

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