Hydrochloric Acid → 1-Methyl-4-(5,5,5-trifluoro-3-methylpent-1-en-2-yl)benzene

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Reaction Steps

Under argon, 1.45 ml (4.34 mmol) of a 3 M solution of methylmagnesium iodide in diethyl ether were initially charged in 10 ml of diethyl ether, and 1000 mg (4.34 mmol) of 4,4,4-trifluoro-2-methyl-1-(4-methylphenyl)butan-1-one, dissolved in 5 ml of diethyl ether, were added slowly at 0 C. The reaction mixture was then slowly warmed to room temperature and stirred overnight. The reaction solution was then slowly added to 15 ml of 1 M hydrochloric acid and diluted with diethyl ether. After removal of the organic phase, the aqueous phase was extracted three more times with diethyl ether. The combined organic phases were dried over magnesium sulfate and filtered, and the solvent was removed under reduced pressure. The crude product was purified chromatographically on silica gel (mobile phase cyclohexane/ethyl acetate 50:1). This gave 710 mg (3.11 mmol, 71% of theory) of the title compound as a colorless oil.

Provenance & Evidence