Methyl iodide → HCID 20230961, compound

Participants

Reaction Conditions

Reaction Steps

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.

Provenance & Evidence