Synthesis of 1,3,5-Trialkylbenzenes from Anils of Methyl Alkyl Ketones

Article abstract of DOI:10.1021/jo00335a046

Besides the previously observed 2,2,4-trialkyl-1,2-dihydroquinolines, a mixture of 1,3,5-trialkylbenzenes and 1-methyl-2,3,5-trialkylbenzenes was obtained in up to 50percent yields when methyl alkyl ketones, aniline, and an acidic catalyst, such as hydrogen chloride, were heated to 180 deg C and the water was removed as formed.The reaction is thought to proceed through an α,β,γ,δ-unsaturated anil intermediate, but the corresponding α,β,γ,δ-unsaturated imines and aliphatic amines did not give trialkylbenzenes.