Potassium Permanganate → 3,4-Dimethoxy-5-nitrobenzoic acid

HRID 1708377Notes

Reaction equation

HRID 1708377 reaction equation
[Mn]([O-])(=O)(=O)=[O:2].[K+].[CH3:7][O:8][C:9]1[CH:10]=[C:11]([CH:14]=[C:15]([N+:19]([O-:21])=[O:20])[C:16]=1[O:17][CH3:18])[CH:12]=[O:13]>O.CC(C)=O>[CH3:7][O:8][C:9]1[CH:10]=[C:11]([CH:14]=[C:15]([N+:19]([O-:21])=[O:20])[C:16]=1[O:17][CH3:18])[C:12]([OH:2])=[O:13]

Participants

5

Reactant 2

HCID 516875Potassium PermanganateHCID 108675653,4-Dimethoxy-5-nitrobenzaldehyde

Product 1

HCID 219286243,4-Dimethoxy-5-nitrobenzoic acidYield 71.6%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent2×HCID 962WaterSolvent

Procedure

To a solution of potassium permanganate (3.05 g) in water (100 ml) was added to a solution of 3,4-dimethoxy-5-nitrobenzaldehyde (2.7 g) in acetone (80 ml). The mixture was then stirred at 20° for 18h whereupon the acetone was evaporated and the residue acidified (2N HCl) and was then decolourised by the addition of sodium metabisulphite sodium. The mixture was then extracted with ethyl acetate (3×200 ml) and the dried extracts evaporated to give the title compound as a colourless solid (2.08 g) m.p. 197°-198°.

Workup

  1. customwas evaporated
  2. additionwas then decolourised by the addition of sodium metabisulphite sodium
  3. extractionThe mixture was then extracted with ethyl acetate (3×200 ml)
  4. customthe dried extracts evaporated

Sources & evidence

ORD record
ord-bd36894982dd4cf4b0877b01bf41f994
Source dataset
uspto-grants-1994_10
Patent number
US05358948

Reaction notes

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