HCID 58609527, compound → Bicyclo[3.2.2]non-6-ene-2,4-dione

HRID 502921Notes

Reaction equation

HRID 502921 reaction equation
Cl[CH:2]1[C:8](=[O:9])[CH:7]2[CH2:10][CH2:11][CH:4]([CH:5]=[CH:6]2)[C:3]1=[O:12]>[Zn].C(O)(=O)C>[CH:7]12[CH2:10][CH2:11][CH:4]([CH:5]=[CH:6]1)[C:3](=[O:12])[CH2:2][C:8]2=[O:9]

Participants

4

Reactant 1

HCID 58609527HCID 58609527, compound

Product 1

HCID 58609528Bicyclo[3.2.2]non-6-ene-2,4-dioneYield 93.2%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
95 °C

Procedure

0.19 g (1 mmol) of 3-chloro-bicyclo[3.2.2]non-6-ene-2,4-dione is treated in the presence of 4 ml of acetic acid with 0.27 g (4 mmol) of zinc and the mixture is heated for 3 hours at a temperature of 95° C. The cooled reaction mixture is then extracted with ethyl acetate against water and then washed again with saturated sodium chloride solution. 0.14 g of amorphous bicyclo[3.2.2]non-6-ene-2,4-dione is obtained as tautomeric form Da.

Workup

  1. customThe cooled reaction mixture
  2. extractionis then extracted with ethyl acetate against water
  3. washwashed again with saturated sodium chloride solution

Sources & evidence

ORD record
ord-bce7b9445e5443cebaf441424205e6d1
Source dataset
uspto-grants-2010_08
Patent number
US07776888B2

Reaction notes

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