Ethanol → (4-Vinylphenyl)acetonitrile

HRID 1593353Notes

Reaction equation

HRID 1593353 reaction equation
[C-:1]#[N:2].[Na+].O.C(O)C.Cl[CH2:9][C:10]1[CH:17]=[CH:16][C:13]([CH:14]=[CH2:15])=[CH:12][CH:11]=1>C(OCC)C>[C:1]([CH2:9][C:10]1[CH:17]=[CH:16][C:13]([CH:14]=[CH2:15])=[CH:12][CH:11]=1)#[N:2]

Participants

6

Reactant 4

HCID 702EthanolHCID 962WaterHCID 8929Sodium Cyanide2×HCID 74126p-Vinylbenzyl chloride

Product 1

HCID 3944539(4-Vinylphenyl)acetonitrile

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
40 °C

Procedure

As shown in the following Reaction 1a, 49.01 g of sodium cyanide (NaCN), 70.07 g of water and 50.96 g of ethanol were added into a 500 ml 4-neck flask equipped with a mechanical stir, and the temperature of the solution was elevated to 60° C. to completely dissolve NaCN. To the solution, 87.50 g of 4-chloromethylstyrene was slowly added and the reaction was carried out for 3 hours at the temperature of 60-70° C. After completion of the reaction, the solution was cooled to 40° C., 100 g of diethylether was added to the solution, and the diethylether layer was separated. The separated organic layer was extracted with 300 g of water three times. The water layer was extracted with 50 g of diethylether and the diethylether extract was added to the organic layer. The separated organic layer was dried with magnesium sulfate for one day, and then the organic solvent was removed using an evaporator to obtain 4-cyanomethylstyrene of deep purple color. The yield of the product was 80%.

Workup

  1. additionwere added into a 500 ml 4-neck flask
  2. customequipped with a mechanical stir
  3. customAfter completion of the reaction
  4. customthe diethylether layer was separated
  5. extractionThe separated organic layer was extracted with 300 g of water three times
  6. extractionThe water layer was extracted with 50 g of diethylether
  7. extractionthe diethylether extract
  8. additionwas added to the organic layer
  9. dry with materialThe separated organic layer was dried with magnesium sulfate for one day
  10. customthe organic solvent was removed
  11. customan evaporator

Sources & evidence

ORD record
ord-5de0b74dcdc14fd484c2f719fabc7930
Source dataset
uspto-grants-2007_11
Patent number
US07297463B2

Reaction notes

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