3-Hydroxyacetophenone → 1-[3-(3-Phenylpropoxy)phenyl]ethan-1-one

HRID 17887

Reaktionsgleichung

Reaktionsgleichung von HRID 17887
[OH:1][C:2]1[CH:3]=[C:4]([C:8](=[O:10])[CH3:9])[CH:5]=[CH:6][CH:7]=1.Br[CH2:12][CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.[I-].[Na+]>[C:15]1([CH2:14][CH2:13][CH2:12][O:1][C:2]2[CH:3]=[C:4]([C:8](=[O:10])[CH3:9])[CH:5]=[CH:6][CH:7]=2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Komponenten

6

Edukt 3

HCID 84873-HydroxyacetophenoneHCID 11430Potassium CarbonateHCID 12503(3-Bromopropyl)benzene

Produkt 1

HCID 214224401-[3-(3-Phenylpropoxy)phenyl]ethan-1-oneAusbeute 94,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 5238Sodium IodideKatalysatorHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

3′-Hydroxyacetophenone (6.81 g, 50 mmol) and 1-bromo-3-phenyl propane (11.95 g, 60 mmol) were dissolved in dimethylformamide (70 ml). Then, potassium carbonate (15 g) and sodium iodide (0.5 g) were added thereto and the mixture was allowed to react for 7 hours at 80° C. Ethyl acetate (300 ml) and purified water (200 ml) were further added to the reaction mixture prior to stirring for 30 min. The organic layer extracted with ethyl acetate was dried over anhydrous magnesium sulfate, concentrated, and the resulting residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:5) to obtain the title compound (12.0 g, yield 94.2%) as a gel.

Aufarbeitung

  1. customto react for 7 hours at 80° C
  2. customEthyl acetate (300 ml) and purified water (200 ml)
  3. additionwere further added to the reaction mixture
  4. extractionThe organic layer extracted with ethyl acetate
  5. dry with materialwas dried over anhydrous magnesium sulfate
  6. concentrationconcentrated
  7. customthe resulting residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:5)

Quellen und Nachweise

ORD-Eintrag
ord-4521dbc84ec14ce1a4ca820a0481d911
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07741323B2

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