Methyl iodide → 2-Methyl-2-phenylcyclohexanone

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.

1. custom2-Methyl-2-phenyl-cyclohexanone was prepared
2. temperaturewas then cooled to −60° C
3. temperatureto warm to room temperature over 12 hours
4. extractionthe mixture was extracted twice with ether
5. extractionThe combined ether extract
6. washwas washed with aqueous sodium sulfite solution and brine
7. dry with materialdried (sodium sulfate)
8. customevaporated to an oil which
9. customwas purified by flash chromatography (5% ethyl acetate-hexane)

ORD record

ord-f5f663653441413aa334383a0804cca0

Source dataset

uspto-grants-2007_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07223767B2