ALKYLATION OF PHENOL BY 1-DODECENE AND 1-DECANOL - A LITERATURE CORRECTION

A recent literature report that 1-dodecene reacts with phenol in the presence of sulfated zirconium oxide (superacid), or 1-dodecanol with phenol in the precsence of H-Mordenite (zeolite), to afford mostly parasubstituted alkylphenols has been shown to be incorrect. The product with zirconium is a mixture of ortho/para isomers (almost-equal-to 50-65/50-35), and not the exclusive para isomer as reported. The major product in the case of zeolite catalysis is the o-alkylphenol, with a high degree of end attachment, and not the predominantly claimed para isomers. The selectivity obtained with H-Mordenite during alkylation of phenol differs from the alkylation of alkylbenzenes and anisole, and is best explained on the basis of a surface catalysis phenomenon.