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1-Pentanol → 2-(2,3-Dimethoxyphenoxy)acetophenone

HRID 3682
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 3682
C(O)CCCC.[CH3:7][O:8][C:9]1[C:14]([O:15][CH3:16])=[CH:13][CH:12]=[CH:11][C:10]=1[OH:17].Br[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[C:25](=[O:27])[CH3:26].C(=O)([O-])[O-].[K+].[K+]>C([O-])(=O)C.[Cu+2].C([O-])(=O)C.C(OCC)(=O)C>[CH3:7][O:8][C:9]1[C:14]([O:15][CH3:16])=[CH:13][CH:12]=[CH:11][C:10]=1[O:17][CH2:26][C:25]([C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:19]=1)=[O:27]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 62761-PentanolHCID 11430Potassium CarbonateHCID 750602'-BromoacetophenoneHCID 788282,3-Dimethoxyphenol

Produkt 1

HCID 183799552-(2,3-Dimethoxyphenoxy)acetophenoneAusbeute 87 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8895
Cupric acetate
Katalysator
HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
150 °C

Versuchsvorschrift

Amyl alcohol (44 ml) was added to 2,3-dimethoxyphenol (5 g), 2'-bromoacetophenone (7 g), potassium carbonate (6.7 g) and copper acetate (1.1 g), followed by heating and stirring at 150° C. for 8 hours for reacting them together. To the reaction solution was added ethyl acetate (300 ml), and the resulting solution was washed in dilute hydrochloric acid, in water, and in a saturated sodium chloride solution, and dried over anhydrous magnesium sulfate, and the solvents therein were distilled off under reduced pressure. The residue was purified by silica gel column chromatography (developing solvent: hexane:ethyl acetate=8:1), to recover 2-(2,3-dimethoxyphenoxy)acetophenone (7.6 g; yield of 87%). By 1H-NMR (90 MHz, CDCl3), the compound has the peaks shown below.

Aufarbeitung

  1. temperatureby heating
  2. washthe resulting solution was washed in dilute hydrochloric acid, in water
  3. dry with materialin a saturated sodium chloride solution, and dried over anhydrous magnesium sulfate
  4. distillationthe solvents therein were distilled off under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (developing solvent: hexane:ethyl acetate=8:1)

Quellen und Nachweise

ORD-Eintrag
ord-b4abd6c40e154847ac62183456b57efd
Quelldatensatz
uspto-grants-1998_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05734067

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