Acetic Acid → HCID 53839455, compound

Participants

Reaction Steps

p-Chloroacetophenone (31 g.), cyanoacetic acid (25 g.), ammonium acetate (5 g.), glacial acetic acid (5 ml.), and benzene (60 ml.) were refluxed together with water separation for 90 hrs., after which time approximately 9 ml. of water had been collected. Removal of benzene and distillation of the residue gave a fraction, b.p. 115°-125°/1 mm., which was dissolved in chloroform (100 ml.) and washed with saturated sodium hydrogen carbonate solution (50 ml.) and water (50 ml.), and dried over sodium sulphate. The extract was evaporated to a viscous oil under reduced pressure and the residual oil was distilled under high vacuum to give β-methyl-p-chlorocinnamonitrile 17.5 g. (49%), b.p. 106°-113°/0.5 mm., λmax. (EtOH) 271 nm (ε 19350) (Found: C, 57.8; H, 4.7; Cl, 19.7; N, 8.1. C10H8ClN requires C, 67.6; H, 4.5; Cl, 20.0; N, 7.9%).

Provenance & Evidence