Water → 4-Cyanobenzoic acid

HRID 2304093Notes

Reaction equation

HRID 2304093 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]>[Ru](Cl)(Cl)Cl>[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

7

Reactant 5

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

Product 1

HCID 120874-Cyanobenzoic acidYield 106.1%

Reagents, catalysts & solvents 1

HCID 61850Ruthenium trichlorideCatalyst

Procedure

A mixture containing p-cyanobenzylamine (13.2 g), water (50 g), and ruthenium trichloride (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 20 minutes. The pH of the mixture was adjusted to four through addition of 98 wt. % sulfuric acid. Precipitated crystals were collected through filtration, washed with water, and dried, to thereby obtain 10.4 g of p-cyanobenzoic acid (yield 76%, based on p-cyanobenzylamine). High performance liquid chromatographic analysis revealed that the p-cyanobenzoic acid obtained had a purity of 95%.

Workup

  1. stirringThe reaction mixture was further stirred for one hour
  2. customPrecipitated crystals
  3. filtrationwere collected through filtration
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-788cbbfa78f04d5fa2ad7a33053fac2a
Source dataset
uspto-grants-2002_08
Patent number
US06433211B1

Reaction notes

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