2-Methyl-2-butene → 2-methoxy-5-(trifluoromethoxy)benzoic Acid

HRID 379488Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 379488
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:8]([O:11][C:12]([F:15])([F:14])[F:13])=[CH:7][C:4]=1[CH:5]=[O:6].CC(=CC)C.O.P([O-])(O)(O)=[O:23].[Na+].Cl([O-])=O.[Na+].[OH-].[Na+]>C(O)(C)(C)C.O.C(OCC)(=O)C.CCCCCC>[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:8]([O:11][C:12]([F:13])([F:14])[F:15])=[CH:7][C:4]=1[C:5]([OH:23])=[O:6]

Komponenten

9

Edukt 5

HCID 105532-Methyl-2-buteneHCID 14798Sodium HydroxideHCID 516949Sodium Phosphate, Monobasic, MonohydrateHCID 27833642-Methoxy-5-(trifluoromethoxy)benzaldehydeHCID 23668197Sodium Chlorite

Produkt 1

HCID 27752862-methoxy-5-(trifluoromethoxy)benzoic Acid

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6386tert-ButanolLösungsmittelHCID 21226206Ethyl acetate hexaneLösungsmittel

Versuchsvorschrift

According to the method of Heterocycles, 16, 2091 (1981), combine 2-methoxy-5-trifluoromethoxybenzaldehyde (0.58 g, 2.65 mmol) and 2-methylbut-2-ene (37 mL) in t-butanol (16 mL). Add dropwise a solution of sodium dihydrogen phosphate hydrate (0.92 g) and sodium chlorite (0.42 g, 4.7 mmol) in water (10 mL). After 4 hours, adjust the pH of the reaction mixture to about 8 to 9 using a 1M aqueous sodium hydroxide solution. Evaporate the reaction mixture invacuo at about ambient temperature to remove most of the t-butanol. Add water (40 mL) and extract three times with hexane (10 mL). Adjust the pH of the aqueous layer to about 1 using a 1M aqueous hydrochloric acid solution and extract five times with diethyl ether. Combine the organic layers, dry over Na2SO4, filter, and evaporate invacuo to give a residue. Chromatograph the residue on silica gel eluting with 1/1 ethyl acetate/hexane containing 0.5% acetic acid to give 2-methoxy-5-trifluoromethoxybenzoic acid: Rf=0.34 (silica gel, 1/1 ethyl acetate/hexane containing 0.5% acetic acid).

Aufarbeitung

  1. customEvaporate the reaction mixture invacuo at about ambient temperature
  2. customto remove most of the t-butanol
  3. extractionAdd water (40 mL) and extract three times with hexane (10 mL)
  4. extractionextract five times with diethyl ether
  5. dry with materialdry over Na2SO4
  6. filtrationfilter
  7. customevaporate invacuo
  8. customto give a residue

Quellen und Nachweise

ORD-Eintrag
ord-3306ab1018404934bc2bc84d165623a7
Quelldatensatz
uspto-grants-2001_10
Patentnummer
US06297259B1

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