Isopropanol → 2-Cyclohexen-1-one, 2,5,6-trimethyl-

HRID 65802

Reaction equation

HRID 65802 reaction equation
O[CH:2]([CH3:6])[CH2:3][CH:4]=[O:5].[CH2:7]([C:9]([CH2:11]C)=O)[CH3:8].[CH:13](O)(C)C.[OH-].[Na+]>C(O)(=O)C>[CH3:13][C:3]1[C:4](=[O:5])[CH:7]([CH3:8])[CH:9]([CH3:11])[CH2:6][CH:2]=1

Participants

6

Reactant 4

HCID 3776IsopropanolHCID 7288Ethyl ketone2×HCID 78973-HydroxybutanalHCID 14798Sodium Hydroxide

Product 1

HCID 892642-Cyclohexen-1-one, 2,5,6-trimethyl-Yield 47.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 88 g of β-hydroxybutyraldehyde and 150 g of diethyl ketone is added dropwise in the course of one hour to a mixture of 250 g of diethyl ketone, 80 g of isopropanol and 5 g of sodium hydroxide powder which is boiling under reflux. The whole is boiled for another hour under reflux. Neutralization is effected with glacial acetic acid and the aqueous phase is separated. The organic layer is fractionated. 65 g of 2,5,6-trimethyl-2-cyclohexen-1-one having a boiling point of 74° to 76° C. at 12 mm Hg is obtained. The yield is 47% with reference to β-hydroxybutyraldehyde.

Workup

  1. temperatureunder reflux
  2. waitThe whole is boiled for another hour
  3. temperatureunder reflux
  4. customthe aqueous phase is separated

Sources & evidence

ORD record
ord-c16defd56be34a8fba979fa521f18f93
Source dataset
uspto-grants-1978_12
Patent number
US04128728

Linked notes

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