3,4-Dimethoxy-2-nitrobenzaldehyde → 3,4-dimethoxy-2-nitrobenzoic acid

HRID 1019983Notes

Reaction equation

HRID 1019983 reaction equation
[Mn]([O-])(=O)(=O)=[O:2].[K+].[CH3:7][O:8][C:9]1[C:10]([N+:19]([O-:21])=[O:20])=[C:11]([CH:14]=[CH:15][C:16]=1[O:17][CH3:18])[CH:12]=[O:13]>C(O)(=O)C>[CH3:7][O:8][C:9]1[C:10]([N+:19]([O-:21])=[O:20])=[C:11]([CH:14]=[CH:15][C:16]=1[O:17][CH3:18])[C:12]([OH:2])=[O:13]

Participants

4

Reactant 2

HCID 1524373,4-Dimethoxy-2-nitrobenzaldehydeHCID 516875Potassium Permanganate

Product 1

HCID 12522693,4-dimethoxy-2-nitrobenzoic acidYield 81.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Potassium permanganate (0.6 g, 3.8 mmol, 2.0 eq), is added at room temperature to a stirred solution of 3,4-dimethoxy-2-nitro-benzaldehyde (0.4 g, 1.9 mmol, 1.0 eq) in acetic acid (10 mL). After stirring overnight at room temperature, the reaction mixture is quenched with saturated sodium sulfite aqueous solution and extracted with ethyl acetate (3×20 mL). The combined organic layers are dried over sodium sulfate, filtered and concentrated to afford 3,4-dimethoxy-2-nitro-benzoic acid as a white solid (0.35 g, 81% yield).

Workup

  1. customthe reaction mixture is quenched with saturated sodium sulfite aqueous solution
  2. extractionextracted with ethyl acetate (3×20 mL)
  3. dry with materialThe combined organic layers are dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-7b7526d3966a4076b0cace382b3c6b90
Source dataset
uspto-grants-2014_05
Patent number
US08716280B2

Reaction notes

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