Acetic Anhydride → 4-Cyanobenzoic acid

HRID 2304085Notes

Reaction equation

HRID 2304085 reaction equation
C([O:4][C:5](=[O:7])[CH3:6])(=O)C.C([O-])(=O)C.[Na+].[C:13]([C:15]1[CH:23]=[CH:22]C(C(N)=O)=[CH:17][CH:16]=1)#[N:14].[N+]([O-])([N+]([O-])=O)=O>C(O)(=O)C>[C:13]([C:15]1[CH:23]=[CH:22][C:6]([C:5]([OH:4])=[O:7])=[CH:17][CH:16]=1)#[N:14]

Participants

6

Reactant 4

HCID 7918Acetic AnhydrideHCID 25352Nitrogen oxide (N2O4)HCID 76427p-CyanobenzamideHCID 517045Sodium Acetate

Product 1

HCID 120874-Cyanobenzoic acidYield 96%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Acetic acid (30 ml), acetic anhydride (70 ml), sodium acetate (6.2 g), and p-cyanobenzamide (5.0 g) were mixed with stirring under cooling with ice, to thereby obtain a mixture. The mixture was allowed to react while dinitrogen tetroxide gas was introduced thereto at 381 N ml/minute for three 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 4.83 g of p-cyanobenzoic acid (yield 96%, based on p-cyanobenzamide). The p-cyanobenzoic acid obtained had a purity of 97%.

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-f87521b3235d491dbbee188e822abf1b
Source dataset
uspto-grants-2002_08
Patent number
US06433211B1

Reaction notes

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