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

HRID 905287Notes

Reaction equation

HRID 905287 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-7559178416fa48aeb5e9f0f0fe39edd1
Source dataset
uspto-grants-1983_12
Patent number
US04423068

Reaction notes

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