Potassium Nitrate → 4-Methyl-3-nitrobenzotrifluoride

HRID 412079

Reaction equation

HRID 412079 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][CH:3]=1.[N+:12]([O-])([O-:14])=[O:13].[K+].CCCCCC.C(OCC)(=O)C>S(=O)(=O)(O)O>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([F:9])([F:10])[F:11])=[CH:6][C:7]=1[N+:12]([O-:14])=[O:13]

Participants

5

Reactant 3

HCID 24434Potassium NitrateHCID 802304-MethylbenzotrifluorideHCID 21226206Ethyl acetate hexane

Product 1

HCID 14728854-Methyl-3-nitrobenzotrifluorideYield 96%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Procedure

To a solution of 4-methylbenzotrifluoride (18.6 g, 116 mmol) in concentrated sulfuric acid (120 ml) was added dropwise a solution of potassium nitrate (12.9 g, 128 mmol) in concentrated sulfuric acid (60 ml) at room temperature over 15 minutes. After stirring for 2 hours at the same temperature, the reaction mixture was poured into ice water, which was extracted with ethyl acetate, dried over anhydrous sodium sulfate, and solvent was distilled off. The residue obtained was submitted to silica gel column chromatography [hexane-ethyl acetate=8:1] to obtain 22.8 g of title compound as pale yellow liquid. Yield 96%.

Workup

  1. extractionwas extracted with ethyl acetate
  2. dry with materialdried over anhydrous sodium sulfate, and solvent
  3. distillationwas distilled off
  4. customThe residue obtained

Sources & evidence

ORD record
ord-53da0b72a505422f8da21304dfcbc003
Source dataset
uspto-grants-2003_05
Patent number
US06562839B1

Linked notes

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