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Water → Methyl 8-(2-methoxy-5-methylphenyl)-8-oxo-octanoate

HRID 228717
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 228717
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1.Cl([O-])(=O)(=O)=O.[Li+].Cl[C:17]([CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][C:25]([O:27][CH3:28])=[O:26])=[O:18].O>[N+](C)([O-])=O.[O-]S(C(F)(F)F)(=O)=O.[Sc+3].[O-]S(C(F)(F)F)(=O)=O.[O-]S(C(F)(F)F)(=O)=O>[CH3:9][O:8][C:5]1[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][C:4]=1[C:17](=[O:18])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][C:25]([O:27][CH3:28])=[O:26]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 962WaterHCID 77314-MethylanisoleHCID 4586585Methyl 8-chloro-8-oxooctanoateHCID 23665649Lithium perchlorate

Produkt 1

HCID 23078435Methyl 8-(2-methoxy-5-methylphenyl)-8-oxo-octanoateAusbeute 57 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 2734571
Scandium(III) triflate
Katalysator
HCID 6375NitromethaneLösungsmittel

Versuchsvorschrift

4-Methylanisole (732 mg) was dissolved in nitromethane (30 ml) to prepare a solution. Anhydrous lithium perchlorate (3.8 g), methyl 7-chlorocarbonyl-heptanoate (1.28 ml), and scandium triflate (300 mg) were added to the solution, and the mixture was stirred at room temperature for 4 hr. Water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was then washed with water and was dried over anhydrous sodium sulfate. The solvent was removed by distillation under the reduced pressure, and the residue was purified by column chromatography using acetone-hexane to give methyl 8-(2-methoxy-5-methylphenyl)-8-oxo-octanoate (992 mg, yield 57%).

Aufarbeitung

  1. customto prepare a solution
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe ethyl acetate layer was then washed with water
  4. dry with materialwas dried over anhydrous sodium sulfate
  5. customThe solvent was removed by distillation under the reduced pressure
  6. customthe residue was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-ad03cac5cb004447ad3c5fe4302f02d4
Quelldatensatz
uspto-grants-2009_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07560558B2

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