Phosgene → 4-Cyanobenzoyl chloride

HRID 2304106Notes

Reaction equation

HRID 2304106 reaction equation
[C:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7](O)=[O:8])=[CH:5][CH:4]=1)#[N:2].C(Cl)([Cl:14])=O>C(#N)C>[C:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([Cl:14])=[O:8])=[CH:5][CH:4]=1)#[N:2]

Participants

4

Reactant 2

HCID 6371PhosgeneHCID 120874-Cyanobenzoic acid

Product 1

HCID 801724-Cyanobenzoyl chlorideYield 98%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

p-Cyanobenzoic acid (14.7 g) and acetonitrile (300 ml) were mixed and stirred vigorously while the solvent was refluxed, and phosgene gas (30 g) was introduced to the mixture over four hours. After dry nitrogen gas was introduced to the reaction mixture for one hour, acetonitrile was removed under ambient pressure, and was further removed under reduced pressure through distillation, to thereby obtain 16.2 g of p-cyanobenzoyl chloride (yield 98%, based on p-cyanobenzoic acid). The p-cyanobenzoyl chloride obtained had a purity of 99%.

Workup

  1. temperaturewas refluxed
  2. additionAfter dry nitrogen gas was introduced to the reaction mixture for one hour
  3. customacetonitrile was removed under ambient pressure
  4. customwas further removed under reduced pressure through distillation

Sources & evidence

ORD record
ord-c71779f9b3b84e88b026fa835b4c037f
Source dataset
uspto-grants-2002_08
Patent number
US06433211B1

Reaction notes

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