Sulfuric Acid → 4-Cyanobenzoic acid

HRID 2304095Notes

Reaction equation

HRID 2304095 reaction equation
[C:1]([C:3]1[CH:10]=[CH:9][C:6](CN)=[CH:5][CH:4]=1)#[N:2].[C:11](=[O:14])([O-])[O-:12].[Na+].[Na+].Cl[O-].[Na+].NC(N)=O.S(=O)(=O)(O)O>[Ru](Cl)(Cl)Cl.O.O1CCOCC1>[C:1]([C:3]1[CH:10]=[CH:9][C:6]([C:11]([OH:12])=[O:14])=[CH:5][CH:4]=1)#[N:2]

Participants

9

Reactant 5

HCID 1118Sulfuric AcidHCID 1176UreaHCID 10340Sodium CarbonateHCID 826084-(Aminomethyl)benzonitrileHCID 23665760Sodium Hypochlorite

Product 1

HCID 120874-Cyanobenzoic acidYield 183.5%

Reagents, catalysts & solvents 3

HCID 61850Ruthenium trichlorideCatalystHCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Conditions

Temperature
50 °C

Procedure

A mixture containing p-cyanobenzylamine (13.2 g), dioxane (70 g), sodium carbonate (5.3 g), water (50 g), and ruthenium trichloride (0.1 g) was stirred, and a 14 wt. % aqueous solution (200 g) of sodium hypochlorite was added dropwise thereto over three hours while the inside temperature of a reactor was maintained at 50° C. or lower. The reaction mixture was further stirred for two hours. 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 13.5 g of p-cyanobenzoic acid (yield 92%, based on p-cyanobenzylamine). The p-cyanobenzoic acid obtained had a purity of 96%.

Workup

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

Sources & evidence

ORD record
ord-c2b710c0c3b5487f987b2a044dd7ba5a
Source dataset
uspto-grants-2002_08
Patent number
US06433211B1

Reaction notes

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