Sodium Hydroxide → 5-Trifluoromethoxysalicylic acid

HRID 457949

Reaktionsgleichung

Reaktionsgleichung von HRID 457949
[OH-:1].[Na+].[OH:3][C:4]1[CH:11]=[CH:10][C:9]([O:12][C:13]([F:16])([F:15])[F:14])=[CH:8][C:5]=1[CH:6]=[O:7]>O.[N+]([O-])([O-])=O.[Ag+]>[OH:3][C:4]1[CH:11]=[CH:10][C:9]([O:12][C:13]([F:14])([F:15])[F:16])=[CH:8][C:5]=1[C:6]([OH:1])=[O:7]

Komponenten

5

Edukt 2

HCID 14798Sodium HydroxideHCID 12680582-Hydroxy-5-(trifluoromethoxy)benzaldehyde

Produkt 1

HCID 27751035-Trifluoromethoxysalicylic acidAusbeute 91 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24470Silver NitrateKatalysatorHCID 962WaterLösungsmittel

Versuchsvorschrift

To a stirring solution of NaOH (8.15 g, 203.8 mmol) in water (35 mL, 5.8 M) was added an aq solution of silver nitrate (17.3 g, 101.9 mmol, 35 mL water, 2.9 M). A brownish solid formed. The flask was placed in an ice bath and to the stirring suspension was added 2-hydroxy-5-trifluoromethoxy-benzaldehyde in 500 mg portions (10.0 g, 48.5 mmol). After addition was complete and the reaction was stirred for 10 min in an ice bath, the mixture was filtered and the brownish precipitate was washed with hot water. The combined washings were acidified with conc HCl to pH 1 and the precipitate was collected by vacuum filtration. This solid was then dissolved in ethyl acetate. The ethyl acetate was washed with saturated aq NaCl, dried over Na2SO4, and filtered. The aqueous layer was also extracted with ethyl acetate. This organic layer was washed with saturated aq NaCl, dried over Na2SO4, filtered and concentrated to provide 2-hydroxy-5-trifluoromethoxy-benzoic acid (9.8 g, 91%) as a white solid: Rf 0.38 (20% methanol in dichloromethane); 1H NMR (CDCl3, 300 MHz) δ 10.30 (bs, 1 H), 7.79 (d, J=3.0 Hz, 1 H), 7.41 (dd, J l=9.3 Hz, J2=3.0 Hz, 1 H), 7.05 (d, J=9.0 Hz, 1 H).

Aufarbeitung

  1. customA brownish solid formed
  2. customThe flask was placed in an ice bath and to the stirring suspension
  3. additionAfter addition
  4. filtrationthe mixture was filtered
  5. washthe brownish precipitate was washed with hot water
  6. filtrationthe precipitate was collected by vacuum filtration
  7. dissolutionThis solid was then dissolved in ethyl acetate
  8. washThe ethyl acetate was washed with saturated aq NaCl
  9. dry with materialdried over Na2SO4
  10. filtrationfiltered
  11. extractionThe aqueous layer was also extracted with ethyl acetate
  12. washThis organic layer was washed with saturated aq NaCl
  13. dry with materialdried over Na2SO4
  14. filtrationfiltered
  15. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-17e77e79c67d4325a9e19c0560168a70
Quelldatensatz
uspto-grants-2007_03
Patentnummer
US07189749B2

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