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

HRID 2293527Notes

Reaction equation

HRID 2293527 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([O:11][CH3:12])[CH:3]=1.[N+:13]([O-])([O-:15])=[O:14].[K+]>S(=O)(=O)(O)O>[Cl:1][C:2]1[C:10]([N+:13]([O-:15])=[O:14])=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([O:11][CH3:12])[CH:3]=1

Participants

4

Reactant 2

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

Product 1

HCID 128487494-Chloro-2-methoxy-5-nitrobenzoic acidYield 93.5%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

In a stream of argon, 1.50 g of 4-chloro-2-methoxybenzoic acid was added to 10 ml of sulfuric acid under ice-cooling, and 0.85 g of potassium nitrate was added to the solution in small portions, followed by 2 hours of stirring. After completion of the reaction, the reaction solution was poured on crushed ice, and the thus precipitated product of interest was collected by filtration, washed with methanol and then dried under a reduced pressure to give 1.74 g of 4-chloro-2-methoxy-5-nitrobenzoic acid.

Workup

  1. temperaturecooling
  2. customAfter completion of the reaction
  3. additionthe reaction solution was poured
  4. customon crushed ice
  5. filtrationthe thus precipitated product of interest was collected by filtration
  6. washwashed with methanol
  7. customdried under a reduced pressure

Sources & evidence

ORD record
ord-54a04c0d0bfb4708913a7a34ea3450bb
Source dataset
uspto-grants-1997_11
Patent number
US05686482

Reaction notes

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