Acetic Anhydride → 4-Cyanobenzoic acid

HRID 2304079Notes

Reaction equation

HRID 2304079 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].N([O-])=[O:13].[Na+].C(OC(=O)C)(=O)C>C(O)(=O)C>[C:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:13])=[O:8])=[CH:5][CH:4]=1)#[N:2]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 76427p-CyanobenzamideHCID 23668193Sodium Nitrite

Product 1

HCID 120874-Cyanobenzoic acidYield 92%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
5 °C

Procedure

p-Cyanobenzamide (14.6 g), sodium nitrite (20.7 g), acetic acid (200 ml), and acetic anhydride (20 ml) were mixed and stirred vigorously at 5° C. To the mixture, trifuloroacetic acid (35 g) was added dropwise over three hours, and further stirred vigorously for five hours. The solvent was removed under reduced pressure, and water (300 ml) was added to the residue. The precipitated crystals were collected through filtration, washed with water, and dried, to thereby obtain 13.4 g of p-cyanobenzoic acid (yield 92%). The p-cyanobenzoic acid obtained had a purity of 98%.

Workup

  1. stirringfurther stirred vigorously for five hours
  2. customThe solvent was removed under reduced pressure, and water (300 ml)
  3. additionwas added to the residue
  4. filtrationThe precipitated crystals were collected through filtration
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-67e165182d844b3a8d300324e7adaa5c
Source dataset
uspto-grants-2002_08
Patent number
US06433211B1

Reaction notes

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