Direct Syntheses of Diphenylmethanol Derivatives from Substituted Benzenes and CHCl₃ through Friedel‐Crafts Alkylation and Post‐Synthetic Hydrolysis or Alcoholysis Catalyzed by Alumina

Abstract

The present study reports an innovative finding that alumina containing water or primary alcohol catalyzes the hydrolysis or alcoholysis, respectively, of the product formed through AlCl3‐mediated Friedel‐Crafts alkylation of methyl‐substituted benzenes and CHCl3. The former and later reactions mainly provided hydroxy‐ and alkoxy‐substituted diarylmethanes, respectively, while the reference reactions without alumina provided bisarylchloromethane. This method enables the selective syntheses of diphenylmethanol derivatives with very simple procedures, without expensive reagents and apparatuses. Furthermore, the alumina used in the reaction could be recycled by washing with water and subsequent drying. From the viewpoint of material recycling, this function is very important for the development of sustainable chemical reactions.

A Simple Way to Obtain a Decachloro Derivative of Cobalt Bis(dicarbollide)

“…Since the dichloromethane cation CHCl 2 + is less stable and less reactive than the trichloromethane one, reactions involving it are much less studied. It is known that reactions of CHCl 3 with aromatics in the presence of AlCl 3 proceed according to the electrophilic substitution mechanism through the formation of the [CHCl 2 ] + [AlCl 4 ] − complex at the first stage [47]. At the same time, the reaction with carboranes under similar conditions, due to the hydride nature of the hydrogen atoms, proceeds according to the mechanism of electrophilic-catalyzed nucleophilic substitution, leading to halogen derivatives [40].…”