Benzyl Chloride → Phenylacetonitrile

HRID 328874Notes

Reaction equation

HRID 328874 reaction equation
[CH2:1](Cl)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C-:9]#[N:10].[Na+]>C(#N)C>[C:2]1([CH2:1][C:9]#[N:10])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 7503Benzyl ChlorideHCID 8929Sodium Cyanide

Product 1

HCID 8794Phenylacetonitrile

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 0.635 g. (0.005 mole) benzyl chloride, O.50 g. sodium cyanide (0.010 mole), 0.53 g. (0.0005 mole) compound I (R = --CH2CH2 -O--2CH2CH3), and 15 ml. acetonitrile was stirred at reflux for 3.0 hours, at which time vapor-phase chromatographic analysis of the reaction mixture showed complete consumption of benzyl chloride and formation of phenylacetonitrile as the sole product. The reaction mixture was poured into water and extracted with petroleum ether to afford phenylacetonitrile and recovered catalyst I (82% yield).

Workup

  1. additionA mixture of 0.635 g
  2. temperatureat reflux for 3.0 hours, at which time vapor-phase chromatographic analysis of the reaction mixture
  3. customconsumption of benzyl chloride and formation of phenylacetonitrile as the sole product
  4. additionThe reaction mixture was poured into water
  5. extractionextracted with petroleum ether

Sources & evidence

ORD record
ord-e04b015db6db4d19b6c244930f485d65
Source dataset
uspto-grants-1977_04
Patent number
US04018832

Reaction notes

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