trans-beta-METHYLSTYRENE → Trans-phenylpropylene oxide

HRID 327854Notes

Reaction equation

HRID 327854 reaction equation
[CH3:1]/[CH:2]=[CH:3]/[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.FC(F)(C(F)(F)C(F)(F)F)C([O-])=[O:13]>>[CH:3](=[O:13])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[C:4]1([CH:3]2[O:13][CH:2]2[CH3:1])[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 252325trans-beta-METHYLSTYRENEHCID 4342798Perfluorobutyrate

Product 2

HCID 240BenzaldehydeYield 30%HCID 123339Trans-phenylpropylene oxideYield 70%

Procedure

The metal-catalyzed epoxidation of trans-β-methylstyrene was performed as described in Example 2 with the substitution of [Ru3O(pfb)6 (Et2O)3 ](pfb) (where pfb= perfluorobutyrate) (0.0449 g, 2.3×10-5 moles) as the catalyst. After 6 hours of reaction, the complete oxidation of the substrate produced benzaldehyde (30%) and 1-phenylpropylene oxide (70%).

Workup

  1. customAfter 6 hours of reaction

Sources & evidence

ORD record
ord-66613db6263748c8bb5ae234a7bbfdc5
Source dataset
uspto-grants-1993_12
Patent number
US05274139

Reaction notes

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