Nitroxyl → 2-Octanone

HRID 1244753Notes

Reaction equation

HRID 1244753 reaction equation
N=O.[CH3:3][CH:4]([OH:11])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].[O-]Cl.[Na+]>C1(C)C=CC=CC=1>[CH3:3][C:4](=[O:11])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]

Participants

5

Reactant 3

HCID 945NitroxylHCID 200832-OctanolHCID 23665760Sodium Hypochlorite

Product 1

HCID 80932-OctanoneYield 100%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In a flask 0.072 g (0.05 mmol) of the product from example 1, 2.5 g (19.2 mmol) of 2-octanol, 10 ml of toluene and 2.8 gr of KHCO3 (20% sol.) were added; the heterogeneous mixture was cooled to 10–15° C. then were added 13.2 g of an aqueous solution of NaOCl (10.5%). After 2 hours the crude organic layer was analyzed using GC and 1H-13C-NMR and 100% of 2-octanone was obtained as desired product. The catalyst was recovered by filtration of the crude reaction mixture.

Workup

  1. temperaturethe heterogeneous mixture was cooled to 10–15° C.

Sources & evidence

ORD record
ord-d3d4f29290e24700a96aea1d0a71054c
Source dataset
uspto-grants-2006_10
Patent number
US07122663B2

Reaction notes

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