Methyl iodide → 2-Methyl-2-phenylcyclohexanone

Participants

Reaction Steps

2-Methyl-2-phenyl-cyclohexanone was prepared according to the procedure described by Paquette et al., J. Org. Chem., 54, 5044 (1989). A solution of 2-phenylcyclohexanone (10 g, 57 mmol) in 40 mL of THF was slowly added to a −50° C. solution of lithium diisopropylamide (prepared by addition of 22 mL of 2.5 M n-BuLi (55 mmol) to a solution of 8.4 mL (60 mmol) of diisopropylamine in 75 mL of THF). The resulting solution was stirred with warming to room temperature over 2 hours and was then cooled to −60° C. Iodomethane (4.7 mL, 75 mmol) was added and the mixture was allowed to warm to room temperature over 12 hours. Water was added and the mixture was extracted twice with ether. The combined ether extract was washed with aqueous sodium sulfite solution and brine, dried (sodium sulfate) and evaporated to an oil which was purified by flash chromatography (5% ethyl acetate-hexane) to afford 7 g of 2-methyl-2-phenyl-cyclohexanone as an oil.

Provenance & Evidence