Study of the Reaction of Benzoyl Chloride and Sodium Dicarboxylate under Inverse Phase Transfer Catalysis

Abstract

Abstract The reaction of benzoyl chloride (PhCOCl) and sodium dicarboxylate (R(COONa)2) catalyzed by an inverse-phase-transfer catalyst (IPTC) in the two-phase medium H2O/CH2Cl2 was investigated. Pyridine 1-oxide (PNO) was used as the inverse-phase-transfer catalyst. Ten dicarboxylates, namely oxalate, malonate, maleate, succinate, adipate, nonanedioate, fumarate, phthalate, isophthalate, and terephthalate, were selected for study. In general, the observed mixed products included mono- and bis(benzoyloxycarbonyl) compounds, benzoic anhydride and benzoic acid, depending on the molecular structure of the dicarboxylate ion. Dicarboxylates of four types were classified according to distribution of products. The reaction rate is strongly affected by PhCOCl and R(COONa)2 due to their influence on the distribution of PNO in the organic phase. A mechanistic interpretation of the experimental data is presented.