p-Cyanobenzamide → 4-Cyanobenzoic acid

HRID 2304082Notes

Reaction equation

HRID 2304082 reaction equation
[C:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7](N)=[O:8])=[CH:5][CH:4]=1)#[N:2].F[B-](F)(F)F.N#[O+:18]>C(#N)C>[C:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:18])=[O:8])=[CH:5][CH:4]=1)#[N:2]

Participants

4

Reactant 2

HCID 76427p-CyanobenzamideHCID 11137142Nitrilooxonium tetrafluoroborate

Product 1

HCID 120874-Cyanobenzoic acidYield 95%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

Acetonitrile (20 ml) and p-cyanobenzamide (2.92 g) were placed in a 100-ml three-neck flask disposed in an ice bath. After the solution was cooled, a solution of nitrosonium tetrafluoroborate (2.57 g) in acetonitrile (20 ml) was added dropwise to the solution over five minutes with stirring. When the addition was completed, the solution was further stirred until generation of gas was terminated. The solvent was removed through distillation under reduced pressure, and water (10 ml) was added to the residue. The precipitated crystals were collected through filtration, washed with water, and dried, to thereby obtain 2.77 g of p-cyanobenzoic acid (yield 95%). High performance liquid chromatographic analysis revealed that the p-cyanobenzoic acid obtained had a purity of 99% or more.

Workup

  1. customdisposed in an ice bath
  2. temperatureAfter the solution was cooled
  3. additionWhen the addition
  4. stirringthe solution was further stirred until generation of gas
  5. customwas terminated
  6. customThe solvent was removed through distillation under reduced pressure, and water (10 ml)
  7. additionwas added to the residue
  8. filtrationThe precipitated crystals were collected through filtration
  9. washwashed with water
  10. customdried

Sources & evidence

ORD record
ord-afe9d7bb4d5a4b6190ff417354f22956
Source dataset
uspto-grants-2002_08
Patent number
US06433211B1

Reaction notes

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