Acetic Anhydride → 3-Cyanobenzoic acid

HRID 2304086Notes

Reaction equation

HRID 2304086 reaction equation
C([O:4][C:5](=[O:7])[CH3:6])(=O)C.C([O-])(=O)C.[Na+].[C:13]([C:15]1[CH:16]=C([CH:21]=[CH:22][CH:23]=1)C(N)=O)#[N:14].[N]=O.[N+]([O-])=O>C(O)(=O)C>[C:13]([C:15]1[CH:16]=[C:6]([CH:21]=[CH:22][CH:23]=1)[C:5]([OH:4])=[O:7])#[N:14]

Participants

7

Reactant 5

HCID 7918Acetic AnhydrideHCID 769743-CyanobenzamideHCID 145068Nitric OxideHCID 517045Sodium AcetateHCID 178526396Nitrogen Dioxide

Product 1

HCID 158753-Cyanobenzoic acidYield 94%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Acetic acid (30 ml), acetic anhydride (70 ml), sodium acetate (6.2 g), and m-cyanobenzamide (5.0 g) were mixed with stirring under cooling with ice, to thereby obtain a mixture. The mixture was allowed to react while the mixed gas of nitrogen monoxide and nitrogen dioxide (volume ratio 1:1) was introduced thereto at 286 N ml/minute for four 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 4.78 g of m-cyanobenzoic acid (yield 94%, based on m-cyanobenzamide). The m-cyanobenzoic acid obtained had a purity of 98%.

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-62078b6c753849dd8153ee34c2ef9764
Source dataset
uspto-grants-2002_08
Patent number
US06433211B1

Reaction notes

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