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

HRID 648666Notes

Reaction equation

HRID 648666 reaction equation
[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]

Participants

5

Reactant 3

HCID 6593Dichloroacetyl chlorideHCID 8471TriethylamineHCID 116051,3-Cyclohexadiene

Product 1

HCID 125073478,8-Dichlorobicyclo[4.2.0]oct-2-en-7-oneYield 70.5%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-277163a41e704a9aa850952c3fe014ca
Source dataset
uspto-grants-1988_04
Patent number
US04735966

Reaction notes

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