Potassium Nitrate → 2,4,5-Trifluoro-3-methyl-6-nitrobenzoic acid

HRID 322821Notes

Reaction equation

HRID 322821 reaction equation
[F:1][C:2]1[C:10]([CH3:11])=[C:9]([F:12])[C:8]([F:13])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[N+:14]([O-])([O-:16])=[O:15].[K+]>S(=O)(=O)(O)O>[F:1][C:2]1[C:10]([CH3:11])=[C:9]([F:12])[C:8]([F:13])=[C:7]([N+:14]([O-:16])=[O:15])[C:3]=1[C:4]([OH:6])=[O:5]

Participants

4

Reactant 2

HCID 24434Potassium Nitrate2×HCID 118055142,4,5-Trifluoro-3-methylbenzoic acid

Product 1

HCID 98375732,4,5-Trifluoro-3-methyl-6-nitrobenzoic acidYield 54.8%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

To 100 ml of conc. sulfuric acid was dissolved 31 g of 2,4,5-trifluoro-3-methylbenzoic acid, and to this solution was incrementally added 19.5 g of potassium nitrate on ice. The solution was stirred at room temperature for 3 days, and another 1.4 g of potassium nitrate was added on ice. After stirring for 6 hours, the solution was poured into ice water, and the solid precipitate was collected by filtration. The precipitate was dissolved in diethylether and washed with water. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was distilled off. The solid precipitate was collected by filtration to obtain 21 g of the title compound.

Workup

  1. stirringAfter stirring for 6 hours
  2. filtrationthe solid precipitate was collected by filtration
  3. dissolutionThe precipitate was dissolved in diethylether
  4. washwashed with water
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled off
  7. filtrationThe solid precipitate was collected by filtration

Sources & evidence

ORD record
ord-1b2087fa5b12426d81f4f2ac0acb7dc1
Source dataset
uspto-grants-2001_04
Patent number
US06211375B1

Reaction notes

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