Benzyl Alcohol → Phenylacetonitrile

HRID 1585554Notes

Reaction equation

HRID 1585554 reaction equation
[CH2:1](O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(Cl)(Cl)=O.[C-:13]#[N:14].[K+]>ClCCl>[CH2:1]([C:13]#[N:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 244Benzyl AlcoholHCID 9032Potassium CyanideHCID 24386Thionyl Chloride

Product 1

HCID 8794PhenylacetonitrileYield 195.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
52.5 °C

Procedure

To a solution of 40.00 g (180 mmoles) of benzyl alcohol in 530 ml of dichloromethane was added within 5 min 32.7 ml (450 mmoles) of thionyl chloride. The solution was evaporated in vacuo to dryness, which was repeated after toluene addition: 46.30 g (106.9%) of crude benzyl chloride, which was dissolved in 230 ml of dimethylformamide and treated with 23.50 g (360 mmoles) of potassium cyanide. The mixture was heated for 4 hours to 50-55° C. The salt was filtered off and the filtrate evaporated in vacuo to dryness, which was repeated after the addition of water, the residue was taken up in ether and extracted with 1N NaOH. The ether phase is evaporated to dryness to yield 41.20 g (99.0%) of crude benzyl cyanide.

Workup

  1. customThe solution was evaporated in vacuo to dryness, which
  2. additionafter toluene addition
  3. dissolution46.30 g (106.9%) of crude benzyl chloride, which was dissolved in 230 ml of dimethylformamide
  4. filtrationThe salt was filtered off
  5. customthe filtrate evaporated in vacuo to dryness, which
  6. additionafter the addition of water
  7. extractionextracted with 1N NaOH
  8. customThe ether phase is evaporated to dryness

Sources & evidence

ORD record
ord-f92779a276a1484281b4de2b57461325
Source dataset
uspto-grants-1999_08
Patent number
US05939422

Reaction notes

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