2-Cyclohexylhepta-1,6-dien-3-ol → 2-Cyclohexyl-1,6-heptadien-3-one

HRID 634979Notes

Reaction equation

HRID 634979 reaction equation
[CH:1]1([C:7]([CH:9]([OH:14])[CH2:10][CH2:11][CH:12]=[CH2:13])=[CH2:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1>CCCCCC.O=[Mn]=O>[CH:1]1([C:7]([C:9](=[O:14])[CH2:10][CH2:11][CH:12]=[CH2:13])=[CH2:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 1

HCID 212616092-Cyclohexylhepta-1,6-dien-3-ol

Product 1

HCID 158978312-Cyclohexyl-1,6-heptadien-3-oneYield 83.9%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 8058HexaneSolvent

Procedure

2-Cyclohexyl-hepta-1,6-dien-3-ol (85 g, 0.44 mol) were oxidized with MnO2 (804 g, 9.2 mol) in 2 l of hexane at RT. After stirring for 96 hours, the reaction mixture was filtered over Celite and concentrated in vacuo yielding 71 g of a yellow oil. Distillation (0.04 Torr/70° C.) yielded 43.5 g (51%) of pure product.

Workup

  1. filtrationthe reaction mixture was filtered over Celite
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-cd81a043ff584f3aa1dd652baf5b7a38
Source dataset
uspto-grants-2001_02
Patent number
US06184419B2

Reaction notes

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