Methyl iodide → 2-Cyclohexen-1-one, 4,4,6-trimethyl-

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Reaction Conditions

Reaction Steps

A solution of 4,4-dimethyl-cyclohex-2-en-1-one (5.00 g, 40.3 mmol, 1 equiv) in tetrahydrofuran (130 mL) was added to a solution of LHMDS (1 M in tetrahydrofuran, 58.4 mL, 58.4 mmol, 1.45 equiv) in tetrahydrofuran (60 mL) at −78° C. After stirring for 1 h, iodomethane (5.02 mL, 80.6 mmol, 2.0 equiv) was added dropwise to the flask. The cooling bath was immediately removed and the reaction mixture was allowed to warm to room temperature (23° C.). After stirring 11 h, saturated aqueous ammonium chloride solution (50 mL) and distilled water (10 mL) were added to the flask. The layers were separated and the aqueous layer was extracted with three 50-mL portions of ether. The combined organic layers were washed once with brine (10 mL) and dried over sodium sulfate (15 min). Following filtration, volatiles were removed in vacuo, leaving a brown residue which was distilled at 22 torr furnishing 4,4,6-trimethyl-cyclohex-2-en-1-one (10, 3.93 g, 72%) as a clear oil, bp 82-86° C. (Torri, J.; Azzaro, M. Bull. Soc. Chem. Fr. 1978, 283; incorporated herein by reference).

Provenance & Evidence