Hydrogen Peroxide → Styrene Oxide

HRID 613781Notes

Reaction equation

HRID 613781 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 54%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

0.0178 g (0.02 mmol) of the complex salt as described in Preparative Example 1 was added to a mixture of 0.208 g (2 mmol) of styrene in 20 ml of CH2Cl2 and 1.68 g (20 mmol) of sodium hydrogen carbonate in 20 ml of water. After a reaction time at room temperature of 10 minutes, 20 ml of H2O2 (30% strength) was added slowly over a period of 2.5 hours, with the temperature rising to 28° C. After a further 22 hours, the reaction was complete. The layers were separated and the organic phase was evaporated under reduced pressure. The product obtained was purified by column chromatography giving styrene oxide in a yield of 54% based on styrene.

Workup

  1. customrising to 28° C
  2. waitAfter a further 22 hours
  3. customThe layers were separated
  4. customthe organic phase was evaporated under reduced pressure
  5. customThe product obtained
  6. customwas purified by column chromatography

Sources & evidence

ORD record
ord-9f21d4fd77b24ef69561a822a662b033
Source dataset
uspto-grants-1999_12
Patent number
US06008387

Reaction notes

Loading…