Methyl iodide → 2,2,5,5-tetramethyl cyclohexanone

HRID 542904Notes

Reaction equation

HRID 542904 reaction equation
[Mg].[CH3:2]I.[CH3:4][CH:5]1[CH2:10][CH2:9][C:8]([CH3:12])([CH3:11])[CH2:7][C:6]1=[O:13]>CCOCC.[Cu]I>[CH3:4][C:5]1([CH3:2])[CH2:10][CH2:9][C:8]([CH3:12])([CH3:11])[CH2:7][C:6]1=[O:13]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 5462224Magnesium2×HCID 1135552333543-18-9

Product 1

HCID 148124172,2,5,5-tetramethyl cyclohexanone

Reagents, catalysts & solvents 2

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

Conditions

Temperature
0 °C

Procedure

5.2 g of magnesium shavings are suspended in 100 ml of absolute ether and treated dropwise with 13.5 ml of methyl iodide. After the addition of 100 ml of ether, the mixture is boiled at reflux for a further 3 hours until all magnesium has dissolved. The mixture is cooled to 0° C. and treated with 20.7 g of finely powdered copper (I) iodide. After stirring at 0° C. for 15 minutes, a solution of 10 g of 3,6,6-trimethyl-2-cyclohexanone in 40 ml of ether is added dropwise thereto and the mixture is stirred at 0° C. for a further 4 hours. Thereafter, the yellow suspension is poured into ice/2N hydrochloric acid, extracted several times with ether, the organic phase is dried and evaporated. The residue is distilled in a water-jet vacuum. There are obtained 9 g of 2,2,5,5-tetramethylcyclohexanone as a colorless liquid, b.p. 71°-74° C./15 mm.

Workup

  1. dissolutionhas dissolved
  2. stirringthe mixture is stirred at 0° C. for a further 4 hours
  3. extractionextracted several times with ether
  4. customthe organic phase is dried
  5. customevaporated
  6. distillationThe residue is distilled in a water-jet vacuum

Sources & evidence

ORD record
ord-6d8270c2174d453f9035e4e4e7d71a2e
Source dataset
uspto-grants-1987_04
Patent number
US04659735

Reaction notes

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