1,7-Octadien-3-ol → 1,7-octadien-3-one

HRID 2286759Notes

Reaction equation

HRID 2286759 reaction equation
[CH2:1]=[CH:2][CH:3]([OH:9])[CH2:4][CH2:5][CH2:6][CH:7]=[CH2:8]>C(Cl)(Cl)(Cl)Cl.[O-2].[O-2].[Mn+4]>[CH2:1]=[CH:2][C:3](=[O:9])[CH2:4][CH2:5][CH2:6][CH:7]=[CH2:8]

Participants

4

Reactant 1

HCID 5457381,7-Octadien-3-ol

Product 1

HCID 118047521,7-octadien-3-oneYield 65.6%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

In 100 cc of carbon tetrachloride is dissolved 3.1 g of 1,7-octadien-3-ol, followed by addition of 10 g of active manganese dioxide. The mixture is stirred at room temperature for 4 days. The reaction mixture is filtered and the solvent is distilled off under a reduced pressure of 20-30 mm Hg. As a fraction at 30°-32° C./4 mm Hg, there is obtained 2 g of 1,7-octadien-3-one. The above fraction is identified to be 1,7-octadien-3-one by the following analyses.

Workup

  1. filtrationThe reaction mixture is filtered
  2. distillationthe solvent is distilled off under a reduced pressure of 20-30 mm Hg

Sources & evidence

ORD record
ord-cd690a4336da4b3c854ca01a4aca03d9
Source dataset
uspto-grants-1981_05
Patent number
US04267377

Reaction notes

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