Potassium Permanganate → 3-Methylbenzene-1,2-dicarboxylic acid

HRID 1751907Notes

Reaction equation

HRID 1751907 reaction equation
[Na+].[Na+].[CH3:3][C:4]1[CH:12]=[CH:11][CH:10]=[C:6]([C:7]([O-:9])=[O:8])[C:5]=1[C:13]([O-:15])=[O:14].[Mn]([O-])(=O)(=O)=O.[K+]>O>[CH3:3][C:4]1[CH:12]=[CH:11][CH:10]=[C:6]([C:7]([OH:9])=[O:8])[C:5]=1[C:13]([OH:15])=[O:14]

Participants

4

Reactant 2

HCID 516875Potassium PermanganateHCID 20818087HCID 20818087, compound

Product 1

HCID 353573-Methylbenzene-1,2-dicarboxylic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

3-Methylphthalic acid disodium salt (4.4 mmol) was dissolved in water (50 ml). Potassium permanganate (14.7 mmol) was added and the resulting solution was stirred for 18 h at room temperature. A precipitate was formed. The precipitate was filtered off and washed three times with hot water. The combined aqueous phase was evaporated under reduced pressure to approximately one third of the initial volume and cooled in an ice-bath. Concentrated HCl was added carefully for neutralization. Expected precipitation of hemimellitic acid did not occur. After evaporation of water in vacuo, the dark residue represented a complex mixture of compounds.

Workup

  1. customA precipitate was formed
  2. filtrationThe precipitate was filtered off
  3. washwashed three times with hot water
  4. customThe combined aqueous phase was evaporated under reduced pressure to approximately one third of the initial volume
  5. temperaturecooled in an ice-bath
  6. additionConcentrated HCl was added carefully for neutralization
  7. customExpected precipitation of hemimellitic acid
  8. customAfter evaporation of water in vacuo
  9. additiona complex mixture of compounds

Sources & evidence

ORD record
ord-9daf975bb25e468298bcdf45df0d7bb3
Source dataset
uspto-grants-2015_10
Patent number
US09162960B2

Reaction notes

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