Sodium Hydroxide → HCID 18329114, compound

Participants

Reaction Steps

To a 500 ml round bottom flask equipped with magnetic stirrer, nitrogen inlet, thermometer and addition funnel was charged 20 g (0.5 moles) of powdered sodium hydroxide, 110 (0.5 moles) of trimethyl sulfoxonium iodide, and 200 mls of anhydrous DMSO. The mixture was then stirred at ambient temperature for 30 minutes. The mixture was then cooled to 15° C., and a solution of 1-cyclopropyl-3-(3-hydroxyphenyl)-2-propene-1-one (47 g, 0.25 moles) was added dropwise in 50 mls of DMSO. The reaction was stirred for 2 hours at 10-15° C., then allowed to warm to ambient temperature, and stirred for an additional 16 hours. The reaction mixture was the quenched with 200 mls of 0.1 N HCl, and extracted with 3×100 mls of ethyl ether. The combined ether extracts were washed successively with 2×100 mls of water, and 100 mls of saturated aqueous sodium chloride solution. The ether extract was then dried over anhydrous magnesium sulfate, filtered and concentrated to dryness under reduced pressure with a rotary evaporator at 45° C. to afford 32 g of the title compound, 2-(3-hydroxyphenyl)cyclopropyl cyclopropyl ketone, as a thick amber oil that crystallized upon standing in a 64% isolated yield.

Provenance & Evidence