Synthesis of hexylnaphthalene, characterization of the products and the reaction mechanism

The structures of the compounds in the reaction of naphthalene with 1-bromohexane catalyzed by aluminium chloride were characterized by gas chromatography/mass spectrometry (GC/MS) and the reaction mechanisms, especially the side reaction, were discussed. The main products include three kinds of linear mono-hexyl-naphthalenes (1-(beta)naphthythexane, 2-(beta)naphthylhexane, and 3-(beta)naphthylhexane) and 10 linear di-hexylnaphthalenes. The by-products mainly are tetralin, mono-hexyltetralin, isohexane, and hexylbenzene. The alkylation of naphthalene with bromohexane was a typical Friedel-Crafts reaction and the side reactions were the disproportionation reaction of naphthalene, tetralin, and 1-bromohexane.