1,2-Dimethoxyethane → 4-[N,N-bis(3,4-dimethylphenyl)amino]styrene

Participants

Reaction Steps

12.1 g of sodium hydride and 580 mL of 1,2-dimethoxyethane were placed in a three-neck flask. While stirring at room temperature, 108.5 g of tetramethylphosphonium bromide was added. After adding one drop of anhydrous ethanol, the mixture was reacted for 4 hours at 70° C. 100 g of 4-[N,N-bis-(3,4-dimethylphenyl)amino]benzaldehyde was added to the reaction mixture. The mixture was reacted for 5 hours at 70° C. The reaction solution was filtered, and an ether extract of filtered cake and filtrate were washed in water. The ether solution was dehydrated with calcium chloride, the ether was removed, and a reaction mixture was obtained. This mixture was recrystallized twice with ethanol, and a needle-form 4-[N,N-bis-(3,4-dimethylphenyl)amino]styrene was obtained. The yield was 84.5 g (yield rate of 85.0%).

Provenance & Evidence