Nitric Acid → 3-Nitro-4-(trifluoromethoxy)benzoic acid

HRID 1859748Notes

Reaction equation

HRID 1859748 reaction equation
[F:1][C:2]([F:14])([F:13])[O:3][C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=[O:9])=[CH:6][CH:5]=1.[N+:15]([O-])([OH:17])=[O:16].O>S(=O)(=O)(O)O>[N+:15]([C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][C:4]=1[O:3][C:2]([F:13])([F:14])[F:1])[C:8]([OH:10])=[O:9])([O-:17])=[O:16]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 962WaterHCID 676134-(Trifluoromethoxy)benzoic acid

Product 1

HCID 186262173-Nitro-4-(trifluoromethoxy)benzoic acid

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

A suspension of 4-trifluoromethoxybenzoic acid (TCI, Portland, Oreg.) (1.0 g, 4.9 mmol) in concentrated sulfuric acid (3 mL) was stirred under an inert atmosphere at room temperature until a solution was obtained. Fuming nitric acid (1 mL) was added dropwise. After 20 hours the mixture was poured into water (100 mL) and stirred. After an hour the precipitate was filtered off, rinsed with water and dried to afford the product (0.8 g); m.p. 137-139° C.

Workup

  1. customwas obtained
  2. stirringstirred
  3. filtrationAfter an hour the precipitate was filtered off
  4. washrinsed with water
  5. customdried

Sources & evidence

ORD record
ord-adf3b2cd83ec4446a97797ef43ebe658
Source dataset
uspto-grants-2003_03
Patent number
US06528528B2

Reaction notes

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