Synthesis of 4-hydroxymethylbenzophenone by phase transfer catalytic method

Abstract

An important organic intermediate 4-hydroxymethylbenzophenone was synthesized by halogenation and hydrolyzation with phase transfer catalytic method using 4-methylbenzophenone as raw material and the technological conditions of reactions were investigated as well. Experimental results show that N-bromosuccinimide (NBS) is a good reagent to give 4-bromomethylbenzophenone undergoing a radical reaction with 4-methylbenzophenone with the yield of about 70.7%; 4-bromomethylbenzophenone can be hydrolyzed under basic conditions in the presence of phase transfer catalyst triethylbenzylammonium chloride for 5 h to give 4-hydrox-ymethylbenzophenone with yield of 84.4%. After the crude product is recrystallized from tetrahydrofuran (THF), the final product is obtained with purity above 99%. The structure of the titled compound is determined by infrared spectrum(IR), proton nuclear magnetic resonance (HNMR), and mass spectrum (MS) and elemental analysis (EA).

Keywords

phase transfer catalytic method, 4-hydroxymethylbenzophenone, mass spectrum, nuclear magnetic resonance