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

HRID 65805

Reaction equation

HRID 65805 reaction equation
C(C(C)=[O:4])=C.C1(C=CC(O)=CC=1)O.[CH3:14][O-:15].[Na+].CC(O[CH2:21][C:22]1[C:35]2[C:30](=[CH:31]C=C[CH:34]=2)[C:29](COC(C)=O)=[C:28]2[C:23]=1[CH:24]=[CH:25]C=C2)=O>C(C(CC)=O)C.O>[CH3:21][C:22]1[C:35](=[O:4])[CH:30]([CH3:31])[CH2:29][CH2:28][C:23]=1[CH3:24].[CH3:28][CH:23]1[CH2:24][CH2:25][C:14](=[O:15])[CH:21]=[C:22]1[CH2:35][CH3:34]

Participants

8

Reactant 4

HCID 785HydroquinoneHCID 6570Methyl vinyl ketoneHCID 613145Acetic acid 10-acetoxymethyl-anthracen-9-ylmethyl esterHCID 10942334Sodium Methoxide

Product 2

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 7288Ethyl ketoneSolvent

Procedure

A mixture of 70 g of methyl vinyl ketone, 10 g of water and 0.1 g of hydroquinone is dripped in the course of one hour into a mixture of 400 g of diethyl ketone and 10 g of a 30% by weight methanolic solution of sodium methylate which is boiling under reflux. The whole is then heated for another two hours under reflux. The mixture obtained is neutralized with glacial acetic and then filtered. Excess diethyl ketone and the water present are distilled off and the residue is fractionated in vacuo. 81 g of 2,3,6-trimethyl-2-cyclohexen-1-one having a boiling point of 89° C. at 12 mm Hg and 9 g of 4-methyl-3-ethyl-2-cyclohexen-1-one having a boiling point of 102° C. at 12 mm Hg are obtained. The total yield of cyclohexenone is 65% with reference to methyl vinyl ketone.

Workup

  1. temperatureunder reflux
  2. temperatureThe whole is then heated for another two hours
  3. temperatureunder reflux
  4. customThe mixture obtained
  5. filtrationfiltered
  6. distillationExcess diethyl ketone and the water present are distilled off

Sources & evidence

ORD record
ord-b41c8aabc0ed4695882d0191604779f4
Source dataset
uspto-grants-1978_12
Patent number
US04128728

Linked notes

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