Collect. Czech. Chem. Commun. 1987, 52, 2936-2945

Friedel-Crafts chloroethylation of hexamethylbenzene

Jaromír Mindla and Giovanni Vittorio Sebastianib

a Department of Organic Chemistry, Institute of Chemical Technology, 532 10 Pardubice, Czechoslovakia
b Dipartimento di Chimica, Universita di Perugia, 06100 Perugia, Italy


The reaction of hexamethylbenzene I with 1,2-dichloroethane in the presence of aluminium chloride gives 1-(2-chloroethyl)-1,2,3,4,5,6-hexamethylbenzenium salt (II) which is decomposed with water. The decomposition products include hexamethylbenzene (I), 3-(2-chloroethyl)-1,2,3,4,5-pentamethyl-6-methylene-1,4-cyclohexadiene (IIIa), 5-(2-chloroethyl)-1,2,3,4,5-pentamethyl-6-methylene-1,3-cyclohexadiene (IIIb), and 1-(2-chloroethyl)-2,3,4,5,6-pentamethylbenzene (IV). The compounds IIIa and IIIb are rearranged into 1-(3-chloropropyl)-2,3,4,5,6-pentamethylbenzene (V).