Potassium Nitrate → 2-Nitro-5-(trifluoromethoxy)benzoic acid

HRID 1246636

Reaktionsgleichung

Reaktionsgleichung von HRID 1246636
[F:1][C:2]([F:14])([F:13])[O:3][C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][CH:12]=1)[C:7]([OH:9])=[O:8].[N+:15]([O-])([O-:17])=[O:16].[K+]>S(=O)(=O)(O)O.CCOC(C)=O>[N+:15]([C:10]1[CH:11]=[CH:12][C:4]([O:3][C:2]([F:13])([F:14])[F:1])=[CH:5][C:6]=1[C:7]([OH:9])=[O:8])([O-:17])=[O:16]

Komponenten

5

Edukt 2

HCID 24434Potassium NitrateHCID 660963-(Trifluoromethoxy)benzoic acid

Produkt 1

HCID 219046132-Nitro-5-(trifluoromethoxy)benzoic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1118Sulfuric AcidLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of 3-trifluoromethoxybenzoic acid (49.0 g, 0.24 mol) in sulfuric acid (500 mL) at less than 0° C. (ice-MeOH bath) was added a solution of potassium nitrate (31.3 g, 0.31 mol) in sulfuric acid (200 mL) over 20 minutes. The resulting solution was stirred at 0° C. for 2 hours, then warmed to room temperature and stirred for 18 hours. The reaction was poured into ice and the resulting acidic solution was extracted with EtOAc (5×). The combined organics were washed with H2O (1×), brine (2×), H2O (1×) and brine (1×), dried (Na2SO4), filtered and concentrated in vacuo to give the crude sub-title compound (65.7 g) as a solid contaminated with HOAc. The crude sub-title compound was dissolved in EtOAc and toluene and concentrated in vacuo to give a HOAc free solid (58.4 g, 97%) that was used in the next step without further purification.

Aufarbeitung

  1. temperaturewarmed to room temperature
  2. stirringstirred for 18 hours
  3. additionThe reaction was poured into ice
  4. extractionthe resulting acidic solution was extracted with EtOAc (5×)
  5. washThe combined organics were washed with H2O (1×), brine (2×), H2O (1×) and brine (1×)
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customto give the crude sub-title compound (65.7 g) as a solid contaminated with HOAc
  10. concentrationtoluene and concentrated in vacuo
  11. customto give a HOAc free solid (58.4 g, 97%) that
  12. customwas used in the next step without further purification

Quellen und Nachweise

ORD-Eintrag
ord-2d151f92b9ff41c58507c2ca4bb34a54
Quelldatensatz
uspto-grants-2006_10
Patentnummer
US07129233B2

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