Hydrogen Peroxide → 2-Octanone

HRID 842415Notes

Reaction equation

HRID 842415 reaction equation
[CH3:1][CH:2]([OH:9])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].ON1C(=O)C2=CC=CC=C2C1=O.O=O.OO>C([O-])(=O)C.[Co+2].C([O-])(=O)C.C(#N)C>[CH3:1][C:2](=[O:9])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

7

Reactant 4

HCID 784Hydrogen PeroxideHCID 977OxygenHCID 10665N-HydroxyphthalimideHCID 200832-Octanol2×

Product 1

HCID 80932-OctanoneYield 53%

Reagents, catalysts & solvents 2

HCID 6277Cobalt diacetateCatalystHCID 6342AcetonitrileSolvent

Procedure

A mixture of 5 mmol of 2-octanol, 0.5 mmol of N-hydroxyphthalimide, 0.0005 mmol of cobalt(II) acetate, and 5 ml of acetonitrile was stirred at 75° C. in an oxygen atmosphere (1 atm) for 24 hours. An iodometric analysis of a reaction mixture revealed that hydrogen peroxide was formed in yield of 21% (selectivity: 35%). Separately, a gas chromatographic analysis of the reaction mixture revealed that the conversion rate from 2-octanol was 60%, and 2-octanone was formed in yield of 53%.

Workup

  1. customwas formed in yield of 21% (selectivity: 35%)

Sources & evidence

ORD record
ord-7157c55f9e164e8189ba1a7c3ac5891f
Source dataset
uspto-grants-2002_04
Patent number
US06375922B1

Reaction notes

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