Sodium Iodide → HCID 13019292, compound

Participants

Reaction Steps

To a solution of 1-(2,4-dihydroxy-3-propyl phenyl) ethanone (10.0 g; 0.051 m) in dry methylethyl ketone (100 ml) was added dried anhydrous sodium carbonate (27 g; 5 mol. eq) and sodium iodide (0.5 g). To the stirred suspension was then added α,α'-dibromo-p-xylene (13.5 g; 0.051 m) and the suspension gently heated at reflux for five hours. The cooled suspension was evaporated under reduced pressure, the residue dissolved in water and extracted with dichloromethane (×2). The organic extract was washed with aqueous sodium hydroxide (2N), then water, dried over magnesium sulphate, filtered, and evaporated to dryness under reduced pressure to give a yellow solid. The solid was stirred with ether (200 ml) for 1 hour and filtered to remove any disubstituted impurity. The filtrate was evaporated under reduced pressure to leave a yellow solid. The solid was chromatographed on a U30 Sorbsil solumn using dichloromethane to give a white solid; recrystallised from ethanol, m.p. 98°-99° C.

Provenance & Evidence