Hydrogen Peroxide → Styrene Oxide

HRID 1768399Notes

Reaction equation

HRID 1768399 reaction equation
[CH2:1]=[CH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.CCCCCCCCCCCC.NC(N)=[O:23].C(=O)(O)[O-].[Na+].OO>O.ClCCl.C([O-])(=O)C.[Co+2].C([O-])(=O)C>[CH2:1]1[O:23][CH:2]1[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

9

Reactant 5

HCID 784Hydrogen PeroxideHCID 1176UreaHCID 7501StyreneHCID 8182DodecaneHCID 516892Sodium Bicarbonate

Product 1

HCID 7276Styrene OxideYield 56%

Reagents, catalysts & solvents 3

HCID 6277Cobalt diacetateCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a mechanically stirred solution of styrene (0.01 mol), dodecane (0.001 mol), urea (0.208 mol), sodium bicarbonate (0.003 mol) and cobalt (II) acetate (0.2 mmol) in 10.0 ml of water and 30 ml of dichloromethane at 25° C. is added 30% aqueous hydrogen peroxide (0.5 mol) in three equal portions over a period of 4 hours. After 14 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 14 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-075249e46ad2418ebd62b7f715efa728
Source dataset
uspto-grants-2007_06
Patent number
US07235676B2

Reaction notes

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