Ethylbenzene → Cyclohexene oxide

HRID 1976867Notes

Reaction equation

HRID 1976867 reaction equation
[CH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1.C([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)C.[OH:15]N1C(=O)C2=CC=CC=C2C1=O>[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[Mo].C([O-])(=O)C.[Co+2].C([O-])(=O)C.C(#N)C1C=CC=CC=1>[CH:1]12[O:15][CH:2]1[CH2:3][CH2:4][CH2:5][CH2:6]2.[C:9]1(=[O:15])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1.[CH:1]1([OH:15])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

9

Reactant 3

HCID 7500EthylbenzeneHCID 8079Cyclohexene2×HCID 10665N-Hydroxyphthalimide

Product 3

HCID 7966CyclohexanolYield 2%HCID 7967CyclohexanoneYield 4%HCID 9246Cyclohexene oxideYield 72%

Reagents, catalysts & solvents 3

HCID 6277Cobalt diacetateCatalystHCID 98885Molybdenum carbonyl (Mo(CO)6)CatalystHCID 7505BenzonitrileSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 4 mmol of cyclohexene, 40 mmol of ethylbenzene, 0.4 mmol of N-hydroxyphthalimide, 0.2 mmol of molybdenum hexacarbonyl, 0.004 mmol of cobalt (II) acetate, 200 mg of Molecular Sieve 4A, and 2 ml of benzonitrile 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 cyclohexene was converted, at a rate of 84%, into cyclohexene oxide (yield: 72%), cyclohexanone (yield: 4%), and cyclohexanol (yield: 2%).

Sources & evidence

ORD record
ord-ee40073ffa10457298c7db141433c346
Source dataset
uspto-grants-2001_05
Patent number
US06229023B1

Reaction notes

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