Hydrochloric Acid → Ethyl 2-chloro-2-[2-(4-methylphenyl)hydrazono]-acetate

Participants

Reaction Conditions

Reaction Steps

A solution of 15.2 g. of sodium nitrite in 40 ml. of water is added dropwise to a solution at 0° C. of 21.4 g. of p-toluidine and 400 ml. of 7.5% hydrochloric acid. The suspension of p-toluene diazonium chloride obtained is added dropwise at 5° C. to a mixture consisting of 36.2 g. of 2-chloroacetic acid ethyl ester, 400 ml. of 50% ethanol and 164 g. of sodium acetate. The mixture then is stirred for three hours at 20° C. and extracted with ethyl acetate. The organic phase is concentrated and the residue is treated with petroleum ether. 41 g. of 2-chloro-2-(4-methyl-phenylhydrazono)-acetic acid ethyl ester with a melting point of 100°-101° C., is obtained.

Provenance & Evidence