Benzoyl chloride → Phenylglyoxylonitrile

HRID 894484Notes

Reaction equation

HRID 894484 reaction equation
[C:1]([O-:9])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Na+].C(Cl)(=O)C1C=CC=CC=1.[C-:20]#[N:21].[Na+]>C1S(=O)(=O)CCC1>[C:1]([C:20]#[N:21])(=[O:9])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 8929Sodium CyanideHCID 517055Sodium Benzoate

Product 1

HCID 11953PhenylglyoxylonitrileYield 99.3%

Reagents, catalysts & solvents 1

HCID 31347SulfolaneSolvent

Procedure

72 g (0.5 mol) of sodium benzoate were mixed with 140.6 g (1 mol) of benzoyl chloride and 80 ml of tetramethylene-sulphone and 25 g (0.5 mol) of 98% pure sodium cyanide. After a stirring time of 20 minutes, an exothermic rise in the temperature to 85° C. was observed. It was now easier to stir the mixture. The subsequent reaction time was 2.5 hours at 150°-160° C. Working up gave the following yield: 65 g (99.3% of theory) of benzoyl cyanide; melting point 34° C.

Workup

  1. customAfter a stirring time of 20 minutes
  2. customto 85° C.

Sources & evidence

ORD record
ord-8d7853b80c474c4e975b1407c6ff7772
Source dataset
uspto-grants-1981_08
Patent number
US04284584

Reaction notes

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