Phosphorus oxychloride → 3-Chlorocinnamonitrile

Participants

Reaction Steps

m-Chlorocinnamamide (1.39 g.) was mixed with sodium metabisulphite (0.72 g.) and phosphoryl chloride (3 ml.). The mixture was heated on the steam-bath for 2.5 hr. and the phosphoryl chloride removed under reduced pressure. The residue was washed well with water, leaving slightly impure m-chlorocinnamonitrile (0.744 g., 59.5%). Recrystallisation from aqueous acetone gave m-chlorocinnamonitrile, m.p. 56°-57°, λmax. (EtOH) 226, 270 nm. ε 19000, 22500.

Provenance & Evidence