Hydrochloric Acid → 4-[2-Benzyloxy-4-(1,1-dimethylheptyl)phenyl]-2-butanone

Participants

Reaction Conditions

Reaction Steps

A solution of 3.89 g. (0.010 mol.) of 1-bromo-2-benzyloxy-4-(1,1-dimethylheptyl)benzene in 15 ml. of tetrahydrofuran was slowly added to 0.36 g. (0.015 mol.) of 70-80 mesh magnesium metal. The resultant mixture was refluxed for 20 minutes and was then cooled to -10° C. Cuprous iodide (0.115 g., 0.006 mol.) was added and stirring continued for 10 minutes. To the resultant mixture was slowly added a solution of 0.701 g. (0.010 ml.) of metyl vinyl ketone in 5 ml. of tetrahydrofuran at such a rate that the reaction temperature could be maintained below 0° C. The reaction mixture was stirred for 30 minutes longer (t<0° C.) and then added to 100 ml. of 1 N hydrochloric acid and 100 g. of ice. The quenched reaction was extracted three times with 150 ml. portions of ether. The combined ether extract was washed twice with 100 ml. portions of water, twice with 100 ml. portions of saturated sodium chloride, dried over magnesium sulfate and evaporated to an oil. The oil was purified via column chromatography on 180 g. of silica gel eluted with 20% ether-cyclohexane to yield 1.07 g. (28%) of the title compound as an oil.

Provenance & Evidence