2-Octanol → 2-Octanone

HRID 2226645Notes

Reaction equation

HRID 2226645 reaction equation
C[C@H](CCCC(C)C)C[CH2:4][CH2:5][C@H:6]([CH2:8][CH2:9][CH2:10][C:11]([CH3:13])=[O:12])C.[O-]Cl.[Na+].CC(O)CCCCCC>C(O)(=O)C>[CH3:13][C:11](=[O:12])[CH2:10][CH2:9][CH2:8][CH2:6][CH2:5][CH3:4]

Participants

5

Reactant 3

HCID 200832-OctanolHCID 1810793(6R,10R)-6,10,14-trimethylpentadecan-2-oneHCID 23665760Sodium Hypochlorite

Product 1

HCID 80932-OctanoneYield 95%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Subsequent hydrogenation (H2 /Pd-C) yields the same saturated C-18 alcohol: ##STR22## Other methods used to oxidize 2° alcohol 9 "phytone" include: (a) aqueous NaOCl (bleach) in acetic acid; such conditions give >95% yield of 2-octanone from 2-octanol. See: J. Org. Chem., 45, 2030 (1980).

Workup

  1. customto oxidize 2°

Sources & evidence

ORD record
ord-f7f2ce0ae0354762a5d8f116c7d8d963
Source dataset
uspto-grants-1994_09
Patent number
US05349071

Reaction notes

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