Dichloroacetyl chloride → 7,7-Dichlorobicyclo[3.2.0]hept-2-en-6-one

HRID 1583633Notes

Reaction equation

HRID 1583633 reaction equation
C(N(CC)CC)C.[CH:8]1[CH2:12][CH:11]=[CH:10][CH:9]=1.[Cl:13][CH:14]([Cl:18])[C:15](Cl)=[O:16]>CCCCCC>[Cl:13][C:14]1([Cl:18])[CH:8]2[CH:9]([CH2:10][CH:11]=[CH:12]2)[C:15]1=[O:16]

Participants

5

Reactant 3

HCID 6593Dichloroacetyl chlorideHCID 7612CyclopentadieneHCID 8471Triethylamine

Product 1

HCID 983787,7-Dichlorobicyclo[3.2.0]hept-2-en-6-one

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent2×

Procedure

Over a period of 1.5 hr 21.7 g of dry triethylamine in 200 ml of hexane was added to a vigorously stirred solution mixture of 27.2 g of freshly distilled cyclopentadiene (I), 30.5 g of dichloroacetyl chloride, and 200 ml of hexane (dried over molecular sieves). After stirring for 15 hours under an atmosphere of nitrogen, the reaction mixture was filtered and the filter cake was washed with hexane. The solvent was removed under vacuum, yielding a 35.2 g of liquid, which, when redistilled under vacuum, afforded 30 g of 7,7-dichlorobicyclo(3.2.0)hept-2-en-6-one (II).

Workup

  1. filtrationthe reaction mixture was filtered
  2. washthe filter cake was washed with hexane
  3. customThe solvent was removed under vacuum

Sources & evidence

ORD record
ord-5ed63a15f334484180b285ea57019318
Source dataset
uspto-grants-1985_11
Patent number
US04552898

Reaction notes

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