Hydrochloric Acid → 2,2,5,5-tetramethyl cyclohexanone

HRID 2290501Notes

Reaction equation

HRID 2290501 reaction equation
[Mg].[CH3:2]I.[CH3:4][C:5]1[CH2:10][CH2:9][C:8]([CH3:12])([CH3:11])[C:7](=[O:13])[CH:6]=1.Cl>CCOCC.[Cu]I>[CH3:11][C:8]1([CH3:12])[CH2:9][CH2:10][C:5]([CH3:2])([CH3:4])[CH2:6][C:7]1=[O:13]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 1410332-Cyclohexen-1-one, 3,6,6-trimethyl-HCID 5462224Magnesium

Product 1

HCID 148124172,2,5,5-tetramethyl cyclohexanoneYield 76.2%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 3283Diethyl EtherSolvent3×

Conditions

Temperature
0 °C

Procedure

5.3 g of magnesium shavings are covered with 100 ml of ether and 30.8 g of methyl iodide are added dropwise in such a manner that the mixture boils slightly. After the addition of 100 ml of ether, the mixture is held at reflux temperature for a further 3 hours, cooled by means of an ice-bath and treated with 20.7 g of copper (I) iodide. After stirring for 15 minutes at 0° C., a solution of 10 g of 3,6,6-trimethyl-2-cyclohexenone in 40 ml of ether is added and the mixture is stirred at 0° C. for a further 3 hours. The green suspension is subsequently poured on to ice, acidified with 2N hydrochloric acid and extracted with ether. The insoluble constituents of the organic phase are filtered off, the filtrate is washed with dilute sodium thiosulphate solution, dried and evaporated. After distillation of the crude product, there are obtained 8.5 g of 2,2,5,5-tetramethylcyclohexanone as a colourless liquid of boiling point 60°-67° C./13 mm Hg.

Workup

  1. additionare added dropwise in such a manner that the mixture
  2. temperatureat reflux temperature for a further 3 hours
  3. temperaturecooled by means of an ice-bath
  4. stirringthe mixture is stirred at 0° C. for a further 3 hours
  5. additionThe green suspension is subsequently poured on to ice
  6. extractionextracted with ether
  7. filtrationThe insoluble constituents of the organic phase are filtered off
  8. washthe filtrate is washed with dilute sodium thiosulphate solution
  9. customdried
  10. customevaporated
  11. distillationAfter distillation of the crude product, there

Sources & evidence

ORD record
ord-77b06b796e094fafb3293f2b1c195957
Source dataset
uspto-grants-1986_10
Patent number
US04617146

Reaction notes

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