Methyl iodide → HCID 20230961, compound

HRID 2290502Notes

Reaction equation

HRID 2290502 reaction equation
[CH2:1]([Li])CCC.C(NC(C)C)(C)C.[CH3:13][C:14]1([CH3:23])[CH2:19][CH2:18][C:17]([CH3:21])([CH3:20])[CH2:16][C:15]1=[O:22].CI>COCCOC>[CH3:13][C:14]1([CH3:23])[CH2:19][CH2:18][C:17]([CH3:21])([CH3:20])[CH:16]([CH3:1])[C:15]1=[O:22]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 7912DiisopropylamineHCID 148124172,2,5,5-tetramethyl cyclohexanoneHCID 178418339Butyllithium

Product 1

HCID 20230961HCID 20230961, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

106.9 ml of n-butyl lithium (2 molar in hexane) are added dropwise while cooling with ice to a solution of 21.6 g of diisopropylamine in 340 ml of ethylene glycol dimethyl ether. After stirring for 30 minutes at 0° C., a solution of 23.2 g of 2,2,5,5-tetramethylcyclohexanone in 100 ml of ethylene glycol dimethyl ether is added while cooling with ice. The mixture is stirred at room temperature for a further 45 minutes, again cooled to 0° C. and 213.9 g of methyl iodide are added thereto rapidly. The mixture is stirred at 50° C. for 45 minutes, cooled, poured on to ice and extracted with ether. After washing the organic phase with 5% hydrochloric acid and diluted sodium hydrogen carbonate solution, it is dried over sodium sulphate and evaporated. Distillation of the crude product on a spinning band column gives 13.7 g of 2,2,5,5,6-pentamethylcyclohexanone as a colourless liquid of boiling point 86°-94° C./16 mm Hg.

Workup

  1. temperaturewhile cooling with ice
  2. stirringThe mixture is stirred at room temperature for a further 45 minutes
  3. temperatureagain cooled to 0° C.
  4. stirringThe mixture is stirred at 50° C. for 45 minutes
  5. temperaturecooled
  6. additionpoured on to ice
  7. extractionextracted with ether
  8. washAfter washing the organic phase with 5% hydrochloric acid and diluted sodium hydrogen carbonate solution, it
  9. dry with materialis dried over sodium sulphate
  10. customevaporated
  11. distillationDistillation of the crude product on a spinning band column

Sources & evidence

ORD record
ord-20ca1c5ca9984feaba10921d75241f09
Source dataset
uspto-grants-1986_10
Patent number
US04617146

Reaction notes

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