Di-tert-butyl peroxide → Cyclooctane

HRID 23833

Reaction equation

HRID 23833 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].C(OOC(C)(C)C)(C)(C)C.[CH2:23]1[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1>>[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.[CH2:23]1[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1

Participants

6

Reactant 3

HCID 8033Di-tert-butyl peroxideHCID 9266CyclooctaneHCID 10665N-Hydroxyphthalimide

Product 3

HCID 9266CyclooctaneHCID 10403CyclooctanoneHCID 12766Cyclooctanol

Procedure

2 mmol of N-hydroxyphthalimide and 4 mmol of di-tert-butyl peroxide are added at a temperature of 130° C. to 200 mmol of cyclooctane in a round-bottomed flask having an attached reflux condenser. Air at approximately 15 l/h is passed through the reaction mixture for 8 hours at said temperature. Cyclooctanol is obtained at a selectivity of 15% and cyclooctanone at a selectivity of 43%, at a cyclooctane conversion rate of 51%.

Workup

  1. temperaturean attached reflux condenser

Sources & evidence

ORD record
ord-0e763f365a82438db6bb844e525df0ba
Source dataset
uspto-grants-2005_02
Patent number
US06852893B2

Linked notes

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