Hydrochloric Acid → Bicyclo[4.2.0]octan-7-one, 8,8-dichloro-

Copper (II) sulphate (2.0 g, 8.0 mmol) was dissolved in water (75 ml) and added to zinc dust (30 g). The mixture was stirred for 2 hours. The mixture was filtered and the solid collected, washed twice with acetone and dried under vacuum at 100° C. for 24 hrs. A portion of the activated zinc (8.0 g) was added to a solution of cyclohexene (10 ml, 98.9 mmol) in diethyl ether (180 ml). Trichloroacetyl chloride (10.48 ml, 93.96 mmol) in diethyl ether (20 ml) was added at such a rate to keep the mixture at reflux. After the addition was complete, the mixture was heated to reflux for 4 hrs. The mixture was cooled to room temperature, diluted with diethyl ether (50 ml) and carefully poured into an aqueous saturated solution of sodium bicarbonate. The mixture was acidified with 2N HCl and the organic phase separated. The ether extract was washed with water and then with saturated aqueous sodium bicarbonate. The organic phase was collected, dried (MgSO4) and the solvent removed under reduced pressure. The residue was purified by flash chromatography (silica, EtOAc:Heptane 1:9) to give 8.62 g of the title compound as a clear oil.

1. filtrationThe mixture was filtered
2. customthe solid collected
3. washwashed twice with acetone
4. customdried under vacuum at 100° C. for 24 hrs
5. temperatureat reflux
6. additionAfter the addition
7. temperaturethe mixture was heated
8. temperatureto reflux for 4 hrs
9. customthe organic phase separated
10. extractionThe ether extract
11. washwas washed with water
12. customThe organic phase was collected
13. dry with materialdried (MgSO4)
14. customthe solvent removed under reduced pressure
15. customThe residue was purified by flash chromatography (silica, EtOAc:Heptane 1:9)

ORD record

ord-40673412dce94d1ba49ba5da9b1e0a3f

Source dataset

uspto-grants-2003_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06596900B2