Reaction of Acetone and Mesityl Oxide with Phenol

Abstract

A quantum mechanical study has been carried out on the difference of the attacking position of acetone and mesityl oxide upon phenol to give bisphenol A and a chroman derivative, respectively. When the acetone molecule attacks the oxygen atom of phenol, the reaction is predicted to be reversible. When acetone attacks the para-position of phenol, the reaction becomes irreversible and leads to bisphenol A. When mesityl oxide attacks the oxygen atom of phenol, the intermediate undergoes a cyclization reaction which is irreversible. The HOMO's of the oxygen and ortho-carbon atoms of phenol are in phase with the LUMO's of the attacking carbon atom and carbonyl carbon atom of mesityl oxide, respectively.