Benzyl Chloride → 1-Nitro-2-(2-phenylethenyl)benzene

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Reaction Steps

The triphenylphosphonium salt of benzyl chloride (38.9 g., 0.10 mole) is added to a solution of sodium (3.0 g.) in ethanol (200 ml.). The resulting solution is treated with 2-nitrobenzaldehyde (16 g., 0.10 mole) and stirred overnight. The mixture is filtered, washed with water and extracted with dichloromethane. The extracts are evaporated to a dark residue which is extracted with carbon tetrachloride, then these extracts are concentrated and passed through a column of alumina, eluting with hexane and carbon tetrachloride to give a yellow oil, 2-nitrostilbene.

Provenance & Evidence