4-Chlorophenol → 1-Phenyl-1-(4'-chlorophenoxy)-3,3-dimethyl-butan-2-one

HRID 25965

Reaktionsgleichung

Reaktionsgleichung von HRID 25965
Br[CH:2]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:3](=[O:8])[C:4]([CH3:7])([CH3:6])[CH3:5].[Cl:15][C:16]1[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=1.[Na]>C(OCC)(=O)C.C(O)C>[C:9]1([CH:2]([O:22][C:19]2[CH:20]=[CH:21][C:16]([Cl:15])=[CH:17][CH:18]=2)[C:3](=[O:8])[C:4]([CH3:7])([CH3:6])[CH3:5])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Komponenten

6

Edukt 3

HCID 46844-ChlorophenolHCID 5360545SodiumHCID 134586931-Bromo-3,3-dimethyl-1-phenylbutan-2-one

Produkt 1

HCID 213260281-Phenyl-1-(4'-chlorophenoxy)-3,3-dimethyl-butan-2-oneAusbeute 67 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of 25.4 g (0.1 mole) of 1-bromo-1-phenyl-3,3-dimethyl-butan-2-one in 50 ml of ethyl acetate was added dropwise, at the boil, to a solution of 12.85 g (0.1 mole) of 4-chlorophenol and 2.3 g (0.1 mole) of sodium in 100 ml of ethanol. After boiling for 12 hours under reflux, the sodium bromide which had separated out was filtered off hot. The filtrate was distilled in vacuo and the solid residue which remained was recrystallized from ligroin. 20.2 g (67% of theory) of 1-phenyl-1-(4'-chlorophenoxy)-3,3-dimethyl-butan-2-one of melting point 103° C. were obtained.

Aufarbeitung

  1. temperatureunder reflux
  2. customthe sodium bromide which had separated out
  3. filtrationwas filtered off hot
  4. distillationThe filtrate was distilled in vacuo
  5. customthe solid residue which remained was recrystallized from ligroin

Quellen und Nachweise

ORD-Eintrag
ord-2a6191e666fa47fc92c5b3dc0bd416f8
Quelldatensatz
uspto-grants-1979_04
Patentnummer
US04147791

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