Selenium Dioxide → HCID 642459, compound

HRID 2372914Notes

Reaction equation

HRID 2372914 reaction equation
[CH3:1][C:2]1[C:3](=[O:11])[C:4]([CH3:10])([CH3:9])[CH2:5][C:6](=[O:8])[CH:7]=1.[Se](=O)=[O:13]>O1CCOCC1.O>[CH3:9][C:4]1([CH3:10])[C:3](=[O:11])[C:2]([CH3:1])=[CH:7][C:6](=[O:8])[C:5]1=[O:13]

Participants

5

Reactant 2

HCID 24007Selenium DioxideHCID 62374Ketoisophorone

Product 1

HCID 642459HCID 642459, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

129.4 g of 2,6,6-trimethylcyclohex-2-ene-1,4-dione (from Example 1) were added to a solution of 100 g of selenium dioxide in a mixture of 800 ml of dioxane and 50 ml of water, and the mixture was refluxed for 9 hours with stirring. The precipitate of elemental selenium was then filtered off with suction, and then all the low boilers were removed in a rotary evaporator. The residue was distilled at 125° C./20 mbar. The distillate was melted, mortared with n-hexane and then extracted with 600 ml of n-hexane. The target product crystallized out in the form of yellow needles.

Workup

  1. temperaturethe mixture was refluxed for 9 hours
  2. filtrationThe precipitate of elemental selenium was then filtered off with suction
  3. customall the low boilers were removed in a rotary evaporator
  4. distillationThe residue was distilled at 125° C./20 mbar
  5. extractionextracted with 600 ml of n-hexane
  6. customThe target product crystallized out in the form of yellow needles

Sources & evidence

ORD record
ord-d3a96b325111451185af6fa6df13e2c2
Source dataset
uspto-grants-1992_03
Patent number
US05101032

Reaction notes

Loading…