Oxygen → Cyclooctanone

Reaction equation

ON1[C:6](=O)[C:5]2=[CH:8][CH:9]=[CH:10][CH:11]=[C:4]2[C:3]1=[O:12].[O-]O.C1(C(C)C)C=CC=CC=1.C1CCCCCCC1.O=O>>[CH:3]1([OH:12])[CH2:4][CH2:11][CH2:10][CH2:9][CH2:8][CH2:5][CH2:6]1.[C:3]1(=[O:12])[CH2:4][CH2:11][CH2:10][CH2:9][CH2:8][CH2:5][CH2:6]1

Participants

Reactant 4

HCID 977Oxygen

HCID 9266Cyclooctane

HCID 10665N-Hydroxyphthalimide

HCID 53627471Cumen hydroperoxide

Product 2

HCID 10403Cyclooctanone

HCID 12766Cyclooctanol

Procedure

2 mmol of N-hydroxyphthalimide and 4 mmol of cumene hydroperoxide are added at a temperature of 130° C. to 200 mmol of cyclooctane in a round-bottomed flask having an attached reflux condenser. Oxygen at approximately 15 l/h is passed through the reaction mixture for 8 hours at said temperature. Cyclooctanol is obtained at a selectivity of 17% and cyclooctanone at a selectivity of 46%, at a cyclooctcane conversion rate of 53%.