4-Chlorophenol → 1-(4-Chlorophenoxy)-2-chloro-2-propene

HRID 52308

Reaktionsgleichung

Reaktionsgleichung von HRID 52308
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[Cl:15][C:16]([CH2:18]Cl)=[CH2:17]>CC(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:18][C:16]([Cl:15])=[CH2:17])=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 46844-ChlorophenolHCID 65652,3-DichloropropeneHCID 11430Potassium Carbonate

Produkt 1

HCID 122548641-(4-Chlorophenoxy)-2-chloro-2-propeneAusbeute 98 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

To a mixture of 4-chlorophenol (6.1 g, 47.4 mmol) and potassium carbonate (13.1 g, 94.7 mmol) in acetone (200 mL), 2,3-dichloropropene (6.6 mL, 71 mmol) was added. After heating to reflux the reaction mixture for 48 hours, the reaction mixture was cooled and filtered. The residue was washed with more acetone and the combined filtrates were concentrated in vacuo. The crude pale brown liquid (11.5 g) was chromatographed (silica gel, hexane/ethyl acetate, 85/15) to give 1-(4-chlorophenoxy)-2-chloro-2-propene (8.9 g, 98%) as a white liquid: Anal. Calc'd. for C9H8OCl2 : C, 53.23, H, 3.97. Found: C, 53.09, H, 3.95.

Aufarbeitung

  1. additionwas added
  2. temperatureAfter heating
  3. temperatureto reflux the reaction mixture for 48 hours
  4. temperaturethe reaction mixture was cooled
  5. filtrationfiltered
  6. washThe residue was washed with more acetone
  7. concentrationthe combined filtrates were concentrated in vacuo
  8. customThe crude pale brown liquid (11.5 g) was chromatographed (silica gel, hexane/ethyl acetate, 85/15)

Quellen und Nachweise

ORD-Eintrag
ord-d86c6284680f4dd89004ee407d378b0c
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05616601

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