Alkylation of Phenol by 1-Dodecene and 1-Decanol. A Literature Correction

Article abstract of DOI:10.1246/bcsj.63.3665

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 presence of H-Mordenite (zeolite), to afford mostly para-substituted alkylphenols has been shown to be incorrect.The product with zirconium is a mixture of ortho/para isomers (ca. 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 a lkylation of alkylbenzenes and anisole, and is best explained on the basis of a surface catalysis phenomenon.