Benzhydrol → p-Menth-1-ene oxide

HRID 1976869Notes

Reaction equation

HRID 1976869 reaction equation
[C:1]1([CH3:10])[CH2:6][CH2:5][CH:4]([CH:7]([CH3:9])[CH3:8])[CH2:3][CH:2]=1.C([OH:24])(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>[C:1]12([CH3:10])[O:24][CH:2]1[CH2:3][CH:4]([CH:7]([CH3:9])[CH3:8])[CH2:5][CH2:6]2

Participants

7

Reactant 5

HCID 7037BenzhydrolHCID 7368(Trifluoromethyl)benzeneHCID 10665N-HydroxyphthalimideHCID 21671p-Menth-1-ene2×HCID 36719Hexafluoroacetone trihydrate

Product 1

HCID 524011p-Menth-1-ene oxideYield 42%

Reagents, catalysts & solvents 1

HCID 6277Cobalt diacetateCatalyst

Conditions

Temperature
60 °C

Procedure

A mixture of 3mmol of 1-p-menthene, 15mmol of benzhydrol, 0.3 mmol of N-hydroxyphthalimide, 0.0015 mmol of cobalt (II) acetate, 0.3 mmol of hexafluoroacetone trihydrate, and 3 ml of trifluoromethylbenzene was stirred at 60° C. under an oxygen atmosphere (1 atm) for 12 hours. Gas chromatographic analysis of products in a reaction mixture revealed that 1-p-menthene was converted, at a rate of 63%, into 1-p-menthene oxide (yield: 42%).

Sources & evidence

ORD record
ord-7e136347c7ac4d679d9651a9b3beb389
Source dataset
uspto-grants-2001_05
Patent number
US06229023B1

Reaction notes

Loading…