Methanesulfonic Acid → 3-Cyanobenzoic acid

HRID 2304080Notes

Reaction equation

HRID 2304080 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6](N)=[O:7])#[N:2].N([O-])=[O:13].[Na+].CS(O)(=O)=O>CS(C)=O>[C:1]([C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6]([OH:13])=[O:7])#[N:2]

Participants

5

Reactant 3

HCID 6395Methanesulfonic AcidHCID 769743-CyanobenzamideHCID 23668193Sodium Nitrite

Product 1

HCID 158753-Cyanobenzoic acidYield 88%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

m-Cyanobenzamide (2.92 g), sodium nitrite (2.76 g), and dimethyl sulfoxide (50 ml) were mixed and stirred vigorously at room temperature. To the mixture, methanesulfonic acid (3.95 g) was added dropwise over ten minutes, and further stirred vigorously for three hours. The solvent was removed under reduced pressure, and water (50 ml) was added to the residue. The precipitated crystals were collected through filtration, washed with water, and dried, to thereby obtain 2.57 g of m-cyanobenzoic acid (yield 88%). The obtained m-cyanobenzoic acid had a purity of 96%.

Workup

  1. stirringfurther stirred vigorously for three hours
  2. customThe solvent was removed under reduced pressure, and water (50 ml)
  3. additionwas added to the residue
  4. filtrationThe precipitated crystals were collected through filtration
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-b61ef6609482488da599e61b9a91e646
Source dataset
uspto-grants-2002_08
Patent number
US06433211B1

Reaction notes

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