Sulfuric Acid → 4-Cyanobenzoic acid

HRID 2304078Notes

Reaction equation

HRID 2304078 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+].S(=O)(=O)(O)O>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 1118Sulfuric AcidHCID 76427p-CyanobenzamideHCID 23668193Sodium Nitrite

Product 1

HCID 120874-Cyanobenzoic acidYield 86%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

p-Cyanobenzamide (1.46 g) and acetic acid (20 ml) were mixed and stirred vigorously at room temperature. To the mixture, sodium nitrite (2.07 g), and immediately thereafter, 95 wt. % sulfuric acid (3 g) was added and stirred vigorously for one hour. The acetic acid was removed under reduced pressure, and water (40 ml) was added to the residue. The precipitated crystals were collected through filtration, washed with water, and dried, to thereby obtain 1.26 g of p-cyanobenzoic acid (yield 86%). The p-cyanobenzoic acid obtained had a purity of 95%.

Workup

  1. stirringstirred vigorously for one hour
  2. customThe acetic acid was removed under reduced pressure, and water (40 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-8d484a61909640c6a475a6d6121e3fd8
Source dataset
uspto-grants-2002_08
Patent number
US06433211B1

Reaction notes

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