Potassium Nitrate → 4-Chloro-2-methoxy-5-nitrobenzoic acid

HRID 1059294Notes

Reaction equation

HRID 1059294 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([O:11][CH3:12])[C:5](=[CH:9][CH:10]=1)[C:6]([OH:8])=[O:7].[N+:13]([O-])([O-:15])=[O:14].[K+]>S(=O)(=O)(O)O>[Cl:1][C:2]1[CH:3]=[C:4]([O:11][CH3:12])[C:5](=[CH:9][C:10]=1[N+:13]([O-:15])=[O:14])[C:6]([OH:8])=[O:7]

Participants

4

Reactant 2

HCID 24434Potassium NitrateHCID 936824-Chloro-o-anisic acid

Product 1

HCID 128487494-Chloro-2-methoxy-5-nitrobenzoic acidYield 100.1%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

To a solution of 33 g of 4-chloro-o-anisic acid in sulfuric acid (100 ml) was added 20 g of potassium nitrate under ice-cooling and the resulting mixture was stirred for 2 hours. The reaction mixture was added to ice/water and extracted with ethyl acetate and the organic layer was dried over anhydrous magnesium sulfate. After distilling off the solvent under reduced pressure, 41 g of the title compound was obtained as pale yellow crystals.

Workup

  1. temperaturecooling
  2. extractionextracted with ethyl acetate
  3. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  4. distillationAfter distilling off the solvent under reduced pressure

Sources & evidence

ORD record
ord-4358da7dcdd84af1b779e44316c8ec0a
Source dataset
uspto-grants-2003_02
Patent number
US06518423B1

Reaction notes

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