Vinyl Aromatic Compounds. I. The Vapor Phase Dehydration of Arylmethylcarbinols

Abstract

The vapor phase dehydration of arylmethylcarbinols over activated alumina has been shown to be a versatile and satisfactory method for the preparation of twenty-three varied vinyl aromatic compounds, of which the following have not been previously reported: m-ethylstyrene, 3,5-diethylstyrene, p-t-butylstyrene, p-cyclohexylstyrene, 6-vinyl-1,2,3,4-tetrahydronaphthalene, p-phenoxystyrene, 1-chloro-4-vinylnaphthalene, 2-vinylfluorene, 1-vinylacenaphthene, 2-vinyldiphenylene oxide and 4-chloro-4′-vinylbiphenyl. The intermediate carbinols from which these eleven compounds were prepared are characterized and their preparation from the analogous arylmethyl ketones is described. The Perrier modification of the Friedel-Crafts synthesis is shown to be especially advantageous for the acetylation of alkylbenzenes and thiophene. © 1946, American Chemical Society. All rights reserved.