Water → 2-Chloro-5-methoxy-4-nitrobenzoic acid

HRID 1019767Notes

Reaction equation

HRID 1019767 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[C:5]([O:11][CH3:12])=[CH:4][C:3]=1[CH3:13].[Mn]([O-])(=O)(=O)=[O:15].[K+].[OH2:20]>>[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[C:5]([O:11][CH3:12])=[CH:4][C:3]=1[C:13]([OH:15])=[O:20]

Participants

4

Reactant 3

HCID 962WaterHCID 516875Potassium PermanganateHCID 158645661-Chloro-4-methoxy-2-methyl-5-nitrobenzene

Product 1

HCID 580563702-Chloro-5-methoxy-4-nitrobenzoic acidYield 78%

Procedure

A solution of 1-chloro-4-methoxy-2-methyl-5-nitrobenzene (1 mmol) and potassium permanganate (4 mmol) in water (100 mL) was heated at reflux temperature for 48 hours. The mixture was allowed to cool to room temperature and the pH was adjusted 2. The solution was extracted with EtOAc (2×100 mL), then the combined organic extracts was dried (Na2SO4) and concentrated under reduced pressure to give the title compound (78%) as a solid.

Workup

  1. temperatureat reflux temperature for 48 hours
  2. extractionThe solution was extracted with EtOAc (2×100 mL)
  3. dry with materialthe combined organic extracts was dried (Na2SO4)
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-aede3d0c4c9d410c894cac2d39277c21
Source dataset
uspto-grants-2014_05
Patent number
US08716287B2

Reaction notes

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