Benzhydrol → 1,2-Epoxy-3-octanol

HRID 1976868Notes

Reaction equation

HRID 1976868 reaction equation
[CH2:1]=[CH:2][CH:3]([OH:9])[CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].C([OH:23])(C1C=CC=CC=1)C1C=CC=CC=1.ON1C(=O)C2=CC=CC=C2C1=O.O.O.O.FC(F)(F)C(C(F)(F)F)=O.FC(C1C=CC=CC=1)(F)F>C([O-])(=O)C.[Co+2].C([O-])(=O)C>[O:23]1[CH:2]([CH:3]([OH:9])[CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])[CH2:1]1

Participants

7

Reactant 5

HCID 7037BenzhydrolHCID 7368(Trifluoromethyl)benzeneHCID 10665N-HydroxyphthalimideHCID 188271-Octen-3-Ol2×HCID 36719Hexafluoroacetone trihydrate

Product 1

HCID 102908541,2-Epoxy-3-octanolYield 40%

Reagents, catalysts & solvents 1

HCID 6277Cobalt diacetateCatalyst

Conditions

Temperature
60 °C

Procedure

A mixture of 3mmol of 1-octen-3-ol, 15mmol of benzhydrol, 0.3 mmol of N-hydroxyphthalimide, 0.0015 mmol of cobalt (II) acetate, 0.6 mmol of hexafluoroacetone trihydrate, and 3 ml of trifluoromethylbenzene was stirred at 60° C. under an oxygen atmosphere (1 atm) for 24 hours. Gas chromatographic analysis of products in a reaction mixture revealed that 1-octen-3-ol was converted, at a rate of 43%, into 1,2-epoxy-3-octanol (yield: 40%).

Sources & evidence

ORD record
ord-b76c200635054022a293f89e44cb585f
Source dataset
uspto-grants-2001_05
Patent number
US06229023B1

Reaction notes

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