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

HRID 1422818Notes

Reaction equation

HRID 1422818 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-a8a97262e80f47e3a0a8e87d524322f1
Source dataset
uspto-grants-2015_01
Patent number
US08927542B2

Reaction notes

Loading…