Dichloroacetyl chloride → 8,8-Dichlorobicyclo[4.2.0]oct-2-en-7-one

HRID 648666Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 648666
[CH:1]1[CH2:6][CH2:5][CH:4]=[CH:3][CH:2]=1.[Cl:7][CH:8]([Cl:12])[C:9](Cl)=[O:10].C(N(CC)CC)C>C(OCC)C>[Cl:7][C:8]1([Cl:12])[CH:1]2[CH:2]([CH2:3][CH2:4][CH:5]=[CH:6]2)[C:9]1=[O:10]

Komponenten

5

Edukt 3

HCID 6593Dichloroacetyl chlorideHCID 8471TriethylamineHCID 116051,3-Cyclohexadiene

Produkt 1

HCID 125073478,8-Dichlorobicyclo[4.2.0]oct-2-en-7-oneAusbeute 70,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

A mixture of 34.0 g of cyclohexadiene and 35.0 g of dichloroacetyl chloride in 300 ml of diethyl ether under nitrogen was refluxed while adding 31.5 g of triethylamine dropwise over a period of 3 hours. The mixture was then stirred at room temperature for 20 hours and filtered. The filtrate was washed with brine, 1N hydrochloric acid, saturated sodium bicarbonate and then dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure and the residue distilled to give 32 g of 8,8-dichlorobicyclo[4.2.0]oct-2-en-7-one.

Aufarbeitung

  1. temperaturewas refluxed
  2. filtrationfiltered
  3. washThe filtrate was washed with brine, 1N hydrochloric acid, saturated sodium bicarbonate
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was removed under reduced pressure
  6. distillationthe residue distilled

Quellen und Nachweise

ORD-Eintrag
ord-277163a41e704a9aa850952c3fe014ca
Quelldatensatz
uspto-grants-1988_04
Patentnummer
US04735966

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