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

HRID 1358856Notes

Reaction equation

HRID 1358856 reaction equation
Cl[C:2]1(Cl)[CH:9]2[CH:4]([CH2:5][CH2:6][CH2:7][CH2:8]2)[C:3]1=[O:10]>C(O)(=O)C.C(OCC)C.[Zn]>[CH:9]12[CH2:2][C:3](=[O:10])[CH:4]1[CH2:5][CH2:6][CH2:7][CH2:8]2

Participants

5

Reactant 1

HCID 326596Bicyclo[4.2.0]octan-7-one, 8,8-dichloro-

Product 1

HCID 549083Bicyclo[4.2.0]octan-7-oneYield 86.5%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 176Acetic AcidSolventHCID 3283Diethyl EtherSolvent

Procedure

(1RS,6SR)-8,8-dichlorobicyclo[4.2.0]octan-7-one (preparation 18) (8.60 g, 44.6 mmol) was heated to reflux in acetic acid (100 ml) with zinc dust (29.0 g, 446 mmol). After 4 hrs the mixture was cooled to room temperature, diluted with diethyl ether (200 ml) and washed with 2N NaOH (2×100 ml) and then with saturated aqueous NaHCO3 (4×100 ml). The ether phase was collected, dried (MgSO4) and the solvent was removed under reduced pressure to give 4.79 g of the title compound as a clear oil.

Workup

  1. washwashed with 2N NaOH (2×100 ml)
  2. customThe ether phase was collected
  3. dry with materialdried (MgSO4)
  4. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-c99af70be8324715b61b4ab26568adf6
Source dataset
uspto-grants-2003_07
Patent number
US06596900B2

Reaction notes

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