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

HRID 1651434Notes

Reaction equation

HRID 1651434 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-a4ab25c47acd4f778a9e3ffbc456bf27
Source dataset
uspto-grants-1990_05
Patent number
US04927963

Reaction notes

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