Hydrogen Peroxide → Styrene Oxide

HRID 613782Notes

Reaction equation

HRID 613782 reaction equation
[CH2:1]=[CH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C(=O)([O-])[OH:10].[Na+].OO>C(Cl)Cl.O>[CH2:1]1[O:10][CH:2]1[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 784Hydrogen PeroxideHCID 7501StyreneHCID 516892Sodium Bicarbonate

Product 1

HCID 7276Styrene OxideYield 49.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 0.208 g of styrene (2 mmol) in 10 ml of CH2Cl2 and 1.68 g (20 mmol) of sodium hydrogen carbonate in 20 ml of water together with 0.026 g (0.02 mmol) of the complex salt described in Preparative Example 5 was stirred for 10 minutes at room temperature. 20 ml (200 mmol) of H2O2 (30% strength) was added slowly over a period of 2.5 hours, with the temperature rising to 28° C. The reaction mixture was stirred for a further 22 hours and the organic phase was then separated from the aqueous phase. The organic phase was evaporated under reduced pressure and the residue was purified by column chromatography. This gave styrene oxide in a yield of 49.6%.

Workup

  1. customrising to 28° C
  2. stirringThe reaction mixture was stirred for a further 22 hours
  3. customthe organic phase was then separated from the aqueous phase
  4. customThe organic phase was evaporated under reduced pressure
  5. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-9b4d1d158f694b20bdb6c4903d7d3548
Source dataset
uspto-grants-1999_12
Patent number
US06008387

Reaction notes

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