Water → 4-Cyanobenzoic acid

HRID 2304092Notes

Reaction equation

HRID 2304092 reaction equation
[C:1]([C:3]1[CH:10]=[CH:9][C:6]([CH2:7]N)=[CH:5][CH:4]=1)#[N:2].Cl[O-].[Na+].NC(N)=[O:16].S(=O)(=O)(O)O.[OH2:23]>>[C:1]([C:3]1[CH:10]=[CH:9][C:6]([C:7]([OH:16])=[O:23])=[CH:5][CH:4]=1)#[N:2]

Participants

6

Reactant 5

HCID 962Water2×HCID 1118Sulfuric AcidHCID 1176UreaHCID 826084-(Aminomethyl)benzonitrileHCID 23665760Sodium Hypochlorite

Product 1

HCID 120874-Cyanobenzoic acidYield 123.5%

Procedure

A mixture containing p-cyanobenzylamine (13.2 g), water (50 g), and ferric chloride (0.2 g) was stirred, and a 14 wt. % aqueous solution (200 g) of sodium hypochlorite was added dropwise thereto at room temperature over two hours. The reaction mixture was further stirred for one hour. Subsequently, water (100 g) and urea (4 g) were added to the mixture, and the resultant mixture was further stirred for minutes. The pH of the mixture was adjusted to four through addition of 98 wt. % sulfuric acid. The precipitated crystals were collected through filtration, washed with water, and dried, to thereby obtain 12.1 g of p-cyanobenzoic acid (yield 82%, based on p-cyanobenzylamine). High performance liquid chromatographic analysis revealed that the obtained p-cyanobenzoic acid had a purity of 95%.

Workup

  1. stirringThe reaction mixture was further stirred for one hour
  2. filtrationThe precipitated crystals were collected through filtration
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-b92f3880dcfe42a592258487df0a8080
Source dataset
uspto-grants-2002_08
Patent number
US06433211B1

Reaction notes

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