Benzoyl chloride → Phenylglyoxylonitrile

HRID 1706853Notes

Reaction equation

HRID 1706853 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C-:10]#[N:11].[Na+]>[Cu]>[C:1]([C:10]#[N:11])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 7412Benzoyl chlorideHCID 8929Sodium Cyanide

Product 1

HCID 11953PhenylglyoxylonitrileYield 57.3%

Reagents, catalysts & solvents 1

HCID 23978CopperCatalyst

Procedure

Using apparatus and a procedure such as was used in Example 1, 140.5 grams (1.0 mole) of benzoyl chloride, 55.0 grams (1.1 moles) of sodium cyanide and 20.0 grams of copper filings were charged to a flask and heated under nitrogen, with stirring, to reflux temperature. The reaction mixture was maintained at a temperature ranging from 190° C. to 200° C. for about 4.5 hours. The reaction mixture was then cooled, diluted with 100 ml. toluene and suction filtered. The filtrate was then distilled to produce 75.0 grams (57.3% yield) of benzoyl cyanide having a boiling point of 48° C. at 0.01 mm. Hg. The distilled product became a semi-solid material at room temperature.

Workup

  1. additionwere charged to a flask
  2. temperatureheated under nitrogen
  3. temperatureto reflux temperature
  4. temperatureThe reaction mixture was maintained at a temperature
  5. temperatureThe reaction mixture was then cooled
  6. additiondiluted with 100 ml
  7. filtrationtoluene and suction filtered
  8. distillationThe filtrate was then distilled

Sources & evidence

ORD record
ord-8187663f05ad46609afd655d0b533869
Source dataset
uspto-grants-1980_06
Patent number
US04209462

Reaction notes

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