2-Methyl-2-butene → 2-(Butyl-ethyl-amino)-5-trifluoromethyl-benzoic acid

HRID 604105Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 604105
[CH2:1]([N:5]([CH2:18][CH3:19])[C:6]1[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][C:7]=1[CH:8]=[O:9])[CH2:2][CH2:3][CH3:4].CC(=CC)C.O.O.P([O-])(O)(O)=[O:28].[Na+].Cl([O-])=O.[Na+]>C(O)(C)(C)C.O.C(OCC)(=O)C>[CH2:1]([N:5]([CH2:18][CH3:19])[C:6]1[CH:13]=[CH:12][C:11]([C:14]([F:15])([F:16])[F:17])=[CH:10][C:7]=1[C:8]([OH:28])=[O:9])[CH2:2][CH2:3][CH3:4]

Komponenten

8

Edukt 4

HCID 105532-Methyl-2-buteneHCID 23668197Sodium ChloriteHCID 23673460Sodium Phosphate, Monobasic, DihydrateHCID 866267522-(Butyl-ethyl-amino)-5-trifluoromethyl-benzaldehyde

Produkt 1

HCID 635134462-(Butyl-ethyl-amino)-5-trifluoromethyl-benzoic acidAusbeute 0,1 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6386tert-ButanolLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

2-(Butyl-ethyl-amino)-5-trifluoromethyl-benzaldehyde (1.72 g) is dissolved in a mixed solvent of tert-butanol (8 ml) and water (2 ml), and thereto are added 2-methyl-2-butene (4 ml), sodium dihydrogenphosphate dihydrate (1.37 g) and sodium chlorite (1.82 g) under ice-cooling, and the mixture is stirred for 2 hours. Thereto are added ethyl acetate and a 1N-hydrochloric acid and the mixture is separated, and the organic layer is washed with a saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue is purified by silica gel column chromatography (chloroform:methanol=1:0→9:1) to give 2-(butyl-ethyl-amino)-5-trifluoromethyl-benzoic acid (1.29 mg). MS (m/z): 290 [M+H]+

Aufarbeitung

  1. temperaturecooling
  2. customa 1N-hydrochloric acid and the mixture is separated
  3. washthe organic layer is washed with a saturated brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue is purified by silica gel column chromatography (chloroform:methanol=1:0→9:1)

Quellen und Nachweise

ORD-Eintrag
ord-b05c036477c34a1f937854c866af659a
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07906517B2

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