Acetonitrile → 3-Chlorobenzoyl cyanide

HRID 1836081Notes

Reaction equation

HRID 1836081 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5](Cl)=[O:6].[C:11](#[N:13])C>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([C:5](=[O:6])[C:11]#[N:13])[CH:8]=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 6342AcetonitrileHCID 69252Benzoyl chloride, 3-chloro-

Product 1

HCID 119842783-Chlorobenzoyl cyanideYield 68%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Metachlorobenzoyl chloride (43.8 g, 0.1 mol), cuprous cyanide (29.1 g, 0.13 mol), and acetonitrile (20 mL) in toluene (37 mL) were refluxed for 3 hours, and were cooled to room temperature. Then, insoluble substances were removed through filtration, and the residue was washed with toluene. Solvent in the resulting filtrate was evaporated under reduced pressure, and the residue was distilled to give metachlorophenyloxoacetonitrile (28 g, 68% yield).

Workup

  1. customThen, insoluble substances were removed through filtration
  2. washthe residue was washed with toluene
  3. customSolvent in the resulting filtrate was evaporated under reduced pressure
  4. distillationthe residue was distilled

Sources & evidence

ORD record
ord-6d9b6352e7d04260a4772070a9eb522c
Source dataset
uspto-grants-2004_08
Patent number
US06777224B2

Reaction notes

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