Hydrogen Peroxide → Styrene Oxide

HRID 1768400Notes

Reaction equation

HRID 1768400 reaction equation
[CH2:1]=[CH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.CCCCCCCCCCCC.CN(C)C=[O:24].C(=O)(O)[O-].[Na+].OO>O.C([O-])(=O)C.[Mn+2].C([O-])(=O)C>[CH2:1]1[O:24][CH:2]1[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

8

Reactant 5

HCID 784Hydrogen PeroxideHCID 6228DimethylformamideHCID 7501StyreneHCID 8182DodecaneHCID 516892Sodium Bicarbonate

Product 1

HCID 7276Styrene OxideYield 56%

Reagents, catalysts & solvents 2

HCID 12525Manganous AcetateCatalystHCID 962WaterSolvent

Procedure

To a mechanically stirred solution of styrene (0.01 mol), dodecane (0.001 mol), dimethylformamide (0.208 mol), sodium bicarbonate (0.003 mol) and manganese (II) acetate (0.15 mmol) in 10.0 ml of water at 30° C. is added 30% aqueous hydrogen peroxide (0.45mol) in three equal portions over a period of 3 hours. After 8 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 styrene oxide in 56% yield with selectivity 80%.

Workup

  1. extractionAfter 8 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-73194039e1fd4d22a5fbbfb34860aeb3
Source dataset
uspto-grants-2007_06
Patent number
US07235676B2

Reaction notes

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