Sodium Hydroxide → 4-Amino-4'-methoxystilbene

Participants

Reaction Conditions

Reaction Steps

A mixture of 10.1 g (40 mmol) of (E)-1-methoxy-4-[2-(4-nitrophenyl)ethenyl]-benzene in 70 ml of ethanol and 130 ml of hydrochloric acid (25%) is heated to 110° C. Portionwise, 15 g of tin are added and stirring is continued for 4.5 hours at 110° C. For the working-up, the reaction mixture is cooled and neutralised with a solution of sodium hydroxide. The mixture is transferred to a separatory funnel where it is extracted with dichloromethane. The organic layer is separated, dried over sodium sulfate and evaporated. The residue is triturated in ether and, thereafter, the remaining solid is collected on a filter funnel. There are obtained 6.15 g (69% of theory) of (E)-4-[2-(4-methoxy-phenyl)-vinyl]-phenylamine as a yellow crystals; MS: m/e=226 (M+H)+.

Provenance & Evidence