Hydrochloric Acid → 2-(2-{4-[Bis(4-methylphenyl)amino]phenyl}ethenyl)phenol

Participants

Reaction Steps

To a reaction vessel equipped with an agitation device, a thermometer and a dripping funnel was added 14.8 g of potassium tert-butoxide and 50 ml of tetrahydrofuran, and an aqueous solution of tetrahydrofuran in which 9.90 g of 2-hydroxybenzylphosphonic acid diethyl and 5.44 g of 4-(N,N-bis(4-methylphenyl)amino) benzaldehyde were dissolved was slowly added dropwise to the reaction vessel at room temperature in a nitrogen gas stream, followed by 2 hr reaction at the same temperature. The resultant solution was cooled, added with water, and added with 2N hydrochloric acid solution for acidification. Thereafter, tetrahydrofuran was removed by an evaporator, and the crude product was extracted with toluene. The toluene phase was sequentially washed with water, sodium hydrogen carbonate solution and saturated saline, and dehydrated by the addition of magnesium sulfate. After filtration, toluene was removed to obtain an oily crude product. Then the oily crude product was purified by column chromatography on silica gel, crystallized in hexane, thereby obtaining 5.09 g of 2-hydroxy-4′-(N,N-bis(4-methylphenyl)amino)stilbene (yield=72%, melting point=136.0° C. to 138.0° C.).

Provenance & Evidence