Oxygen → Cyclooctanone

HRID 23832

Reaction equation

HRID 23832 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

6

Reactant 4

HCID 977OxygenHCID 9266CyclooctaneHCID 10665N-HydroxyphthalimideHCID 53627471Cumen hydroperoxide

Product 2

HCID 10403CyclooctanoneHCID 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%.

Workup

  1. temperaturean attached reflux condenser

Sources & evidence

ORD record
ord-c62d3ce4d7174d1fad0761d7168f165f
Source dataset
uspto-grants-2005_02
Patent number
US06852893B2

Linked notes

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