Oligomerization of 3,5-dimethyl benzyl alcohol promoted by clay: Experimental and theoretical study

Abstract

Linear oligomerization of 3,5-dimethyl benzyl alcohol is induced by a montmorillonite clay (Tonsil Optimum Extra), producing 1,3,5,7-tetramethyl-9,10- dihydro-anthracene, which, by loss of protons results in the product 1,3,5,7- tetramethylanthracene. It was also found that the compounds 4-(3′, 5′-dimethylbenzyl)- 1,3,5,7-tetramethyl-9,10-dihydroanthracece and 4-(3′,5′-dimethylbenzyl)-1,3,5,7-tetramethylanthracene were formed from 1,3,5,7-tetramethyl-9,10-dihydroanthracene. 1,3,5,7- Tetramethylanthryl radical cation was formed from 1,3,5,7-tetramethyl-9,10- dihydroanthracene; it was characterized by Electronic Paramagnetic Resonance (EPR). On the other hand, a theoretical analysis was performed, allowing the rationalization of the observed products and some of the key reaction steps. © 2010 licensee MDPI, Basel, Switzerland.