3-Cyclohexen-1-ol, 4-(3-hydroxy-1-butenyl)-3,5,5-trimethyl- → 3-Buten-2-one, 4-(4-hydroxy-2,6,6-trimethyl-1-cyclohexen-1-yl)-, (3E)-

HRID 703619Notes

Reaction equation

HRID 703619 reaction equation
[OH:1][CH:2]1[CH2:7][C:6]([CH3:9])([CH3:8])[C:5]([CH:10]=[CH:11][CH:12]([OH:14])[CH3:13])=[C:4]([CH3:15])[CH2:3]1>CC(C)=O.[O-2].[O-2].[Mn+4]>[OH:1][CH:2]1[CH2:7][C:6]([CH3:8])([CH3:9])[C:5]([CH:10]=[CH:11][C:12](=[O:14])[CH3:13])=[C:4]([CH3:15])[CH2:3]1

Participants

4

Reactant 1

HCID 5289693-Cyclohexen-1-ol, 4-(3-hydroxy-1-butenyl)-3,5,5-trimethyl-

Product 1

HCID 5389533-Buten-2-one, 4-(4-hydroxy-2,6,6-trimethyl-1-cyclohexen-1-yl)-, (3E)-Yield 60.6%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 180AcetoneSolvent

Procedure

In 50 ml of anhydrous acetone was dissolved 2.5 g of 4-(4-hydroxy-2,6,6-trimethylcyclohex-1-enyl)but-3-en-2-ol, and 10.4 g of activated manganese dioxide was added to the solution, followed by heating at 40° to 50° C. for 24 hours while vigorous stirring. After completion of the reaction, the reaction mixture was allowed to cool to room temperature, and any insoluble matter was removed by filtration. The filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography to obtain 1.5 g (yield: 60%) of 4-(4-hydroxy-2,6,6-trimethylcyclohex-1-enyl)but-3-en-2-one.

Workup

  1. additionwas added to the solution
  2. temperatureby heating at 40° to 50° C. for 24 hours while vigorous stirring
  3. customAfter completion of the reaction
  4. customany insoluble matter was removed by filtration
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-88e38adbfa5440afbadce1551d128a14
Source dataset
uspto-grants-1991_01
Patent number
US04983723

Reaction notes

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