Carboxylation of phenol derivatives. 22. Formation of alkali alkyl carbonate by the O-carboxylation of alcohol in the presence of an alkali salt of a weak acid.
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<I>O</I>-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, <I>p</I>-R′C<SUB>6</SUB>H<SUB>4</SUB>OM (R′=CH<SUB>3</SUB>, CH<SUB>3</SUB>O, or Br), Et<SUB>2</SUB>NCSSM, NaCN, and C<SUB>6</SUB>H<SUB>4</SUB>(CO)<SUB>2</SUB>NK (M=K or Na) were effective. The mixture of HOC<SUB>6</SUB>H<SUB>4</SUB>COOM and ROCOOM was obtained from the reaction using MOC<SUB>6</SUB>H<SUB>4</SUB>COOM as an alkali salt. However, the mixture was composed of equimolar amounts of <I>p</I>-HOC<SUB>6</SUB>H<SUB>4</SUB>COOM and ROCOOM when <I>p</I>-MOC<SUB>6</SUB>H<SUB>4</SUB>COOM was used. In this reaction, two mechanisms have been examined.
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