tert-Butyl hydroperoxide → 2-Hexyloxirane

HRID 1678915Notes

Reaction equation

HRID 1678915 reaction equation
[O-]O.[B].[CH3:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH:10]=[CH2:11].C([O:16]O)(C)(C)C>B#[W]>[CH2:11]1[O:16][CH:10]1[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH3:4]

Participants

6

Reactant 4

HCID 6410tert-Butyl hydroperoxideHCID 81251-OcteneHCID 18500Perhydroxyl radicalHCID 5462311Boron

Product 1

HCID 181262-HexyloxiraneYield 36%

Reagents, catalysts & solvents 1

HCID 82793Tungsten borideCatalyst

Conditions

Temperature
90 °C

Procedure

In this example, the liquid phase epoxidation of an olefinic compound with an organic hydroperoxide was carried out in the presence of a catalytic amount of a boron containing substance in accordance with the instant invention. A 250 ml. flask equipped with a stirrer, thermometer, reflux condenser and dropping funnel was charged with 84 g. octene-1 and 1 g. tungsten boride (WB). The charged mixture was heated to 90° C and 90% tertiary butyl hydroperoxide was added dropwise until a total of 25 g. had been added. The reaction mixture was then heated at reflux (108°-110° C) for 220 minutes with stirring. The heated mixture was allowed to cool and then the crude reaction product was analyzed. The analysis indicated a 36% yield of octene oxide based on the amount of charged hydroperoxide. The crude reaction product was filtered by conventional methods and the resulting filtrate was analyzed for metal content by atomic absorption analysis. No metals were detected in the filtrate.

Workup

  1. customflask equipped with a stirrer
  2. temperaturethermometer, reflux condenser
  3. additionwas charged with 84 g
  4. additionhad been added
  5. temperatureThe reaction mixture was then heated
  6. temperatureat reflux (108°-110° C) for 220 minutes
  7. temperatureto cool
  8. customthe crude reaction product

Sources & evidence

ORD record
ord-13c5feaec88143179e0bdc1e31756d09
Source dataset
uspto-grants-1978_03
Patent number
US04077986

Reaction notes

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