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

HRID 703568Notes

Reaction equation

HRID 703568 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 238 g of cyclohexadiene and 245 g of dichloroacetyl chloride in 2 litres of diethyl ether under nitrogen was refluxed while adding 220 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, 1 N 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 224 g of 8,8-dichlorobicyclo[4.2.0]oct-2-en-7-one, the compound of formula (4).

Workup

  1. temperaturewas refluxed
  2. filtrationfiltered
  3. washThe filtrate was washed with brine, 1 N 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-5e031f090b06408182c0fd504daa480b
Source dataset
uspto-grants-1991_01
Patent number
US04983627

Reaction notes

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