tert-Butyl hydroperoxide → Cyclohexanol cyclohexanone

HRID 397370

Reaction equation

HRID 397370 reaction equation
C(OO)(C)(C)C.S([O-])([O-])(=O)=O.[Na+].[Na+].[C:14]1(=[O:20])[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1>C(#N)C.C1CCCCC1>[C:14]1(=[O:20])[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1.[CH:14]1([OH:20])[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1

Participants

6

Reactant 3

HCID 6410tert-Butyl hydroperoxideHCID 7967CyclohexanoneHCID 24436Sodium Sulfate

Product 1

HCID 22492587Cyclohexanol cyclohexanone

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8078CyclohexaneSolvent2×

Procedure

To an argon purged solution of Complex 3 (0.1 mM) in acetonitrile, cyclohexane (50 mM) was added followed by 20 mM of tert-butylhydroperoxide (t-BuOOH) (dissolved in di-t-butylether). The reaction mixture was maintained under an argon atmosphere for 30 min followed by the addition of an aqueous solution of sodium sulphate (0.4 M). The iron complex dissolved in the aqueous phase and the products (cyclohexane and cyclohexanone) were analysed by GC. Analyses yielded 0.5-1.5 mM of cyclohexanone +cyclohexanol (5-15 turnovers).

Workup

  1. temperatureThe reaction mixture was maintained under an argon atmosphere for 30 min
  2. dissolutionThe iron complex dissolved in the aqueous phase

Sources & evidence

ORD record
ord-47d52450d6ea4d3dacc379a5126d1475
Source dataset
uspto-grants-2003_08
Patent number
US06610641B2

Linked notes

Loading…