Reaction of dicarbonates with carboxylic acids catalyzed by weak Lewis acids: general method for the synthesis of anhydrides and esters

…, R Dalpozzo, E Marcantoni, P Melchiorre, L Sambri

Index: Bartoli, Giuseppe; Bosco, Marcella; Carlone, Armando; Dalpozzo, Renato; Marcantoni, Enrico; Melchiorre, Paolo; Sambri, Letizia Synthesis, 2007 , # 22 p. 3489 - 3496

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Citation Number: 28

Abstract

Abstract The reaction between carboxylic acids (RCOOH) and dialkyl dicarbonates [(R 1 OCO) 2 O], in the presence of a weak Lewis acid such as magnesium chloride and the corresponding alcohol (R 1 OH) as the solvent, leads to the esters RCOOR 1 in excellent yields. The mechanism involves a double addition of the acid to the dicarbonate, affording a carboxylic anhydride [(RCO) 2 O], R 1 OH and carbon dioxide. The esters arise from the ...