Isobutyraldehyde → 2-Cyclohexen-1-one, 4,4,6-trimethyl-

HRID 1657678Notes

Reaction equation

HRID 1657678 reaction equation
[CH:1](=[O:5])[CH:2]([CH3:4])[CH3:3].[C:6]([C:9]([CH3:11])=O)([CH3:8])=[CH2:7]>[OH-].[Na+]>[CH3:7][C:6]1([CH3:8])[CH2:3][CH:2]([CH3:4])[C:1](=[O:5])[CH:11]=[CH:9]1

Participants

4

Reactant 2

HCID 6561IsobutyraldehydeHCID 13143Methyl isopropenyl ketone

Product 1

HCID 1145072-Cyclohexen-1-one, 4,4,6-trimethyl-Yield 59%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

The procedure of example III was employed on 12 moles of isobutyraldehyde, 11 moles of methyl isopropenyl ketone and 800 ml of 0.8 M aqueous sodium hydroxide solution. After the reaction was completed the aqueous layer was removed. To the residual organic phase was added an equal volume of benzene and a catalytic amount (ca. 5 g) of p-toluenesulfonic acid. The reaction mixture was heated at reflux with concomitant removal of water via a Dean Stark trap. The usual workup and distillation afforded 897 g (59%) of the desired 4,4,6-trimethyl-2-cyclohexenone (II) with physical constants and spectral data identical with that isolated in Example III. Continued distillation afforded no material containing the 5-hydroxy-2,4,4-trimethylcyclohexanone isolated in Example III where the acid treatment step was omitted.

Workup

  1. customwas removed
  2. additionTo the residual organic phase was added an equal volume of benzene
  3. temperatureThe reaction mixture was heated
  4. temperatureat reflux with concomitant removal of water via a Dean Stark trap
  5. distillationThe usual workup and distillation

Sources & evidence

ORD record
ord-5db9e35a4369498f9e5c631d325ed967
Source dataset
uspto-grants-1976_06
Patent number
US03962148

Reaction notes

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