Hydrogen Peroxide → Indene oxide

HRID 1768396Notes

Reaction equation

HRID 1768396 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.CCCCCCCCCCCC.NC(N)=[O:24].C(=O)(O)[O-].[Na+].OO>O.S([O-])([O-])(=O)=O.[Mn+2]>[CH:1]12[O:24][CH:2]1[CH2:3][C:4]1[C:9]2=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

8

Reactant 5

HCID 784Hydrogen PeroxideHCID 1176UreaHCID 7219IndeneHCID 8182DodecaneHCID 516892Sodium Bicarbonate

Product 1

HCID 92838Indene oxideYield 99%

Reagents, catalysts & solvents 2

HCID 24580Manganese SulfateCatalystHCID 962WaterSolvent

Procedure

To a mechanically stirred solution of indene (0.01 mol), dodecane (0.001 mol), urea (0.208 mol), sodium bicarbonate (0.003 mol) and manganese sulphate (0.1 mmol) in 10.0 ml of water at 20° C. is added 30% aqueous hydrogen peroxide (0.4 mol) in three equal portions over a period of 3 hours. After 10 hours the reaction mixture was extracted with 4×5 ml diethyl ether. The combined organic layer was dried over anhydrous sodium sulphate. Removal of solvent yielded indene oxide in >99% yield with selectivity 95%.

Workup

  1. extractionAfter 10 hours the reaction mixture was extracted with 4×5 ml diethyl ether
  2. dry with materialThe combined organic layer was dried over anhydrous sodium sulphate
  3. customRemoval of solvent

Sources & evidence

ORD record
ord-34a28610e4cd44459ac7d195fff77c7e
Source dataset
uspto-grants-2007_06
Patent number
US07235676B2

Reaction notes

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