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

HRID 1387591Notes

Reaction equation

HRID 1387591 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-9bb80842fbec45f091ad27e45ae46bb9
Source dataset
uspto-grants-2001_07
Patent number
US06268387B1

Reaction notes

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