8,8-Dichlorobicyclo[4.2.0]oct-2-en-7-one → HCID 12507350, compound

HRID 1651435Notes

Reaction equation

HRID 1651435 reaction equation
Cl[C:2]1(Cl)[CH:9]2[CH:4]([CH2:5][CH2:6][CH:7]=[CH:8]2)[C:3]1=[O:10]>C(O)(=O)C.[Zn]>[CH:9]12[CH2:2][C:3](=[O:10])[CH:4]1[CH2:5][CH2:6][CH:7]=[CH:8]2

Participants

4

Reactant 1

HCID 125073478,8-Dichlorobicyclo[4.2.0]oct-2-en-7-one

Product 1

HCID 12507350HCID 12507350, compoundYield 71.1%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalyst2×HCID 176Acetic AcidSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of 1.1 g of 8,8-dichlorobicyclo[4.2.0]oct-2-en-7-one in 10 ml of glacial acetic acid was added 2.0 g of zinc dust in portions over a period of 15 minutes. The mixture was then stirred at 65° C. for 1 hour, then a further 0.5 g of zinc dust was added and the mixture stirred at 75° C. for 1 hour. The mixture was cooled, filtered, the solid washed with hexane, the filtrate and combined washings diluted with water and extracted with hexane. The hexane layer was dried over anhydrous sodium sulfate, the solvent removed under reduced pressure and the residue distilled under vacuum to give 500 mg of bicyclo[4.2.0]oct-2-en-7-one, the compound of formula (III), where X and Y are hydrogen.

Workup

  1. stirringthe mixture stirred at 75° C. for 1 hour
  2. temperatureThe mixture was cooled
  3. filtrationfiltered
  4. washthe solid washed with hexane
  5. additiondiluted with water
  6. extractionextracted with hexane
  7. dry with materialThe hexane layer was dried over anhydrous sodium sulfate
  8. customthe solvent removed under reduced pressure
  9. distillationthe residue distilled under vacuum

Sources & evidence

ORD record
ord-4f05d0ee7c33425abbfff217d41818cf
Source dataset
uspto-grants-1990_05
Patent number
US04927963

Reaction notes

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