Nitric Acid → HCID 18187005, compound

HRID 1357752Notes

Reaction equation

HRID 1357752 reaction equation
[F:1][C:2]([F:13])([F:12])[O:3][C:4]1[CH:11]=[CH:10][C:7]([CH:8]=[O:9])=[CH:6][CH:5]=1.[N+:14]([O-])([OH:16])=[O:15]>S(=O)(=O)(O)O>[N+:14]([C:5]1[CH:6]=[C:7]([CH:10]=[CH:11][C:4]=1[O:3][C:2]([F:12])([F:13])[F:1])[CH:8]=[O:9])([O-:16])=[O:15]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 69573p-(Trifluoromethoxy)benzaldehyde

Product 1

HCID 18187005HCID 18187005, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
0 °C

Procedure

4-Trifluoromethoxybenzaldehyde (1.9 g, 10 mmol) was dissolved in concentrated sulfuric acid (8 mL) at 0 ° C. followed by dropwise addition of 70 % nitric acid (1,1 mL). The reaction mixture was stirred at 0 ° C. for 2 hours, then poured onto ice water and extracted with ethyl acetate. The organic layer was washed with water, aqueous sodium bicarbonate solution , dried (sodium sulfate), filtered and evaporated. The residue was chromatographed on silica gel, eluting with 20 % ethyl acetate/hexane to provide 1.55.g of the title compound.

Workup

  1. additionpoured onto ice water
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water, aqueous sodium bicarbonate solution
  4. dry with materialdried (sodium sulfate)
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was chromatographed on silica gel
  8. washeluting with 20 % ethyl acetate/hexane

Sources & evidence

ORD record
ord-c4c0fa48c8424d41983f7f72b5dff165
Source dataset
uspto-grants-2003_07
Patent number
US06593335B1

Reaction notes

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