Carboxylation of Phenol Derivatives. XXII. Formation of Alkali Alkyl Carbonate by theO-Carboxylation of Alcohol in the Presence of an Alkali Salt of a Weak Acid

Abstract O-Carboxylation of the alcohol (ROH) occurred to give alkali alkyl carbonate in a good yield when carbon dioxide was introduced into the mixture of an alkali salt of a weak acid, alcohol, and acetone (or THF) at room temperature under atmospheric pressure. Such alkali salts as PhOM, p-R′C6H4OM (R′=CH3, CH3O, or Br), Et2NCSSM, NaCN, and C6H4(CO)2NK (M=K or Na) were effective. The mixture of HOC6H4COOM and ROCOOM was obtained from the reaction using MOC6H4COOM as an alkali salt. However, the mixture was composed of equimolar amounts of p-HOC6H4COOM and ROCOOM when p-MOC6H4COOM was used. In this reaction, two mechanisms have been examined.