Acetic Anhydride → 4-Cyanobenzoic acid

HRID 2304083Notes

Reaction equation

HRID 2304083 reaction equation
C([O:4][C:5](=[O:7])[CH3:6])(=O)C.[C:8]([C:10]1[CH:18]=[CH:17]C(C(N)=O)=[CH:12][CH:11]=1)#[N:9].N([N+]([O-])=O)=O>C(O)(=O)C>[C:8]([C:10]1[CH:18]=[CH:17][C:6]([C:5]([OH:4])=[O:7])=[CH:12][CH:11]=1)#[N:9]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 61526Nitrogen trioxideHCID 76427p-Cyanobenzamide

Product 1

HCID 120874-Cyanobenzoic acidYield 94%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Acetic acid (30 ml), acetic anhydride (70 ml), and p-cyanobenzamide (5 g) were mixed with stirring under cooling with ice, to thereby obtain a mixture. The mixture was allowed to react while dinitrogen trioxide gas was introduced thereto at 190 N ml/hour for six hours. The residual solvent was removed through distillation in vacuum, and water was added to the residue, to thereby form crystals. The precipitated crystals were collected through filtration, washed with water, and dried, to thereby obtain 4.73 g of p-cyanobenzoic acid (yield 94%, based on p-cyanobenzamide). High performance liquid chromatographic analysis revealed that the p-cyanobenzoic acid obtained had a purity of 99% or more.

Workup

  1. temperatureunder cooling with ice
  2. customto thereby obtain a mixture
  3. additionwas introduced
  4. customThe residual solvent was removed through distillation in vacuum, and water
  5. additionwas added to the residue
  6. customto thereby form crystals
  7. filtrationThe precipitated crystals were collected through filtration
  8. washwashed with water
  9. customdried

Sources & evidence

ORD record
ord-751cfbd76c6d40b1a7e185722772be8e
Source dataset
uspto-grants-2002_08
Patent number
US06433211B1

Reaction notes

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