Acetonitrile → 3-Cyanobenzoic acid

HRID 2304096Notes

Reaction equation

HRID 2304096 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+]>[O-2].[Fe+2].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 48.3%

Reagents, catalysts & solvents 2

HCID 449809Ferrous oxideCatalystHCID 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 iron 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 4 through addition of sulfuric acid. The precipitated crystals were collected through filtration, washed with water, dried, to thereby obtain 7.1 g of m-cyanobenzoic acid (yield 48%, based on m-cyano-benzylamine). 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 4 through addition of sulfuric acid
  3. filtrationThe precipitated crystals were collected through filtration
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-0d09417caa984748917970256032a775
Source dataset
uspto-grants-2002_08
Patent number
US06433211B1

Reaction notes

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