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Zeolite Catalysts for Phenol Benzoylation with Benzoic Acid: Exploring the Synthesis of Hydroxybenzophenones Gherardo Gliozzi, Sauro Passeri, Francesca Bortolani, Mattia Ardizzi, Patrizia Mangifesta and Fabrizio Cavani Abstract: In this paper, we report on the reaction of phenol benzoylation with benzoic acid, which was carried out in the absence of solvent. The aim of this reaction is the synthesis of hydroxybenzophenones, which are important intermediates for the chemical industry. H-beta zeolites offered superior performance compared to H-Y, with a remarkably high conversion of phenol and high yields to the desired compounds, when using a stoichiometric amount of benzoic acid. It was found that the reaction mechanism did not include the intramolecular Fries rearrangement of the primary product phenyl benzoate, but indeed, the bimolecular reaction between phenyl benzoate and phenol mainly contributed to the formation of hydroxybenzophenones. The product distribution was greatly affected by the presence of Lewis-type acid sites in H-beta; it was suggested that the interaction between the aromatic ring and the electrophilic Al3+ species led to the preferred formation of o-hydroxybenzophenone, because of the decreased charge density on the C atom at the para position of the phenolic ring. H-Y zeolites were efficient than H-beta in phenyl benzoate transformation into hydroxybenzophenones. 1. Introduction The acylation of phenolic compounds is an important class of reactions with several applications in the chemical industry [1,2]. In fact, aromatic hydroxy ketones are intermediates for the synthesis of various pharmaceuticals and fragrances. p-Hydroxyacetophenone and o-hydroxyacetophenone are used for the synthesis of paracetamol and aspirin, respectively; the ortho isomer is also an intermediate for the synthesis of 4-hydroxycoumarin and flavanones. Furthermore, the acylation of resorcinol is an important process for the synthesis of a precursor for the UV-light absorbent for polymers, 4-o-octyl-o-hydroxybenzophenone [3]. In general, these reactions are catalyzed by homogeneous Friedel-Crafts Lewis-type catalysts; however, due to the environmental problems associated with the use of these compounds, alternative heterogeneous systems have been sought Reprinted from Catalysts. Cite as: Gliozzi, G.; Passeri, S.; Bortolani, F.; Ardizzi, M.; Mangifesta, P.; Cavani, F. Zeolite Catalysts for Phenol Benzoylation with Benzoic Acid: Exploring the Synthesis of Hydroxybenzophenones. Catalysts 2015, 5, 2223–2243. 117PDF Image | Zeolite Catalysis
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