Hydroquinone → 2,3,6-Trimethylcyclohex-2-en-1-one

HRID 65806

Reaction equation

HRID 65806 reaction equation
O=[C:2]([CH3:6])[CH2:3][CH2:4][OH:5].[CH2:7]([C:9]([CH2:11]C)=O)[CH3:8].[C:13]1([CH:20]=[CH:19][C:17]([OH:18])=[CH:16][CH:15]=1)O.C[O-].[Na+]>CO>[CH3:13][C:3]1[C:4](=[O:5])[CH:7]([CH3:8])[CH2:9][CH2:11][C:2]=1[CH3:6].[CH3:7][CH:13]1[CH2:20][CH2:19][C:17](=[O:18])[CH:16]=[C:15]1[CH2:2][CH3:3]

Participants

7

Reactant 4

HCID 785HydroquinoneHCID 7288Ethyl ketone2×HCID 1115094-Hydroxy-2-ButanoneHCID 10942334Sodium Methoxide

Product 2

HCID 30168432,3,6-Trimethylcyclohex-2-en-1-oneHCID 125403044-Methyl-3-ethyl-2-cyclohexen-1-one

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 88 g of 3-ketobutan-1-ol, 150 g of diethyl ketone and 0.1 g of hydroquinone is dripped in the course of two hours into a mixture of 250 g of diethyl ketone and 10 g of a 30% by weight solution of sodium methylate in methanol which is boiling under reflux. The reaction mixture is then heated under reflux for another two hours. 37 g of water is removed from the reaction mixture by entrainment during the reaction. The whole is processed as described in Example 8. 73 g of 2,3,6-trimethyl-2-cyclohexen-1-one and 10 g of 4-methyl-3-ethyl-2-cyclohexen-1-one are obtained. The total yield of cyclohexenone is 60% with reference to 3-ketobutan-1-ol.

Workup

  1. temperatureunder reflux
  2. temperatureThe reaction mixture is then heated
  3. temperatureunder reflux for another two hours
  4. custom37 g of water is removed from the reaction mixture by entrainment during the reaction

Sources & evidence

ORD record
ord-5b15879798284a96b75a16ddc57a38f9
Source dataset
uspto-grants-1978_12
Patent number
US04128728

Linked notes

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