Acetonitrile → 3-Cyanobenzoic acid

HRID 2304097Notes

Reaction equation

HRID 2304097 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)CN)#[N:2].C(#N)C.[C:14](=[O:17])([O-])[OH:15].[Na+].S(OOS([O-])(=O)=O)([O-])(=O)=O.[Na+].[Na+]>[Ru]=O.O>[C:1]([C:3]1[CH:10]=[C:9]([CH:8]=[CH:5][CH:4]=1)[C:14]([OH:15])=[O:17])#[N:2]

Participants

7

Reactant 4

HCID 6342AcetonitrileHCID 62655Sodium PersulfateHCID 457594Benzonitrile, 3-(aminomethyl)-HCID 516892Sodium Bicarbonate

Product 1

HCID 158753-Cyanobenzoic acidYield 56%

Reagents, catalysts & solvents 2

HCID 178527103HCID 178527103, compoundCatalystHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A mixture containing m-cyanobenzylamine (13.2 g), acetonitrile (80 g), sodium hydrogencarbonate (76 g), water (500 g), sodium persulfate (95 g), and ruthenium oxide (0.25 g) was stirred for reaction at 80° C. over ten hours. After the precipitated solid was removed through filtration, the pH of the filtrate was adjusted to four through addition of sulfuric acid. The precipitated crystals were collected through filtration, washed with water, and dried, to thereby obtain 8.2 g of m-cyanobenzoic acid (yield 56%, based on m-cyanobenzylamine). The m-cyanobenzoic acid obtained had a purity of 94%.

Workup

  1. customAfter the precipitated solid was removed through filtration
  2. additionthe pH of the filtrate was adjusted to four through addition of sulfuric acid
  3. filtrationThe precipitated crystals were collected through filtration
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-9f7afe34d1ad4429ba31b3470bf4778c
Source dataset
uspto-grants-2002_08
Patent number
US06433211B1

Reaction notes

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