STUDY OF THE REACTION OF BENZOYL CHLORIDE AND SODIUM DICARBOXYLATE UNDER INVERSE PHASE-TRANSFER CATALYSIS

The reaction of benzoyl chloride (PhCOCl) and sodium dicarboxylate (R( COONa)(2)) catalyzed by an inverse-phase-transfer catalyst (IPTC) in t he 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 fo r study, In general, the observed mixed products included mono- and bi s(benzoyloxycarbonyl) compounds, benzoic anhydride and benzoic acid, d epending on the molecular structure of the dicarboxylate ion. Dicarbox ylates of four types were classified according to distribution of prod ucts. The reaction rate is strongly affected by PhCOCl and R(COONa)(2) due to their influence on the distribution of PNO in the organic phas e. A mechanistic interpretation of the experimental data is presented.