Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Convenient Synthesies of Carboxylic Esters and Thiol Esters Using Acid Chlorides and Zinc Chloride

  • Kim, Sung-Gak (Department of Chemistry, Korea Advanced Institute of Science and Technology) ;
  • Lee, Won-Jae (Department of Chemistry, Korea Advanced Institute of Science and Technology) ;
  • Lee, Jae-ln (Department of Chemistry, Korea Advanced Institute of Science and Technology)
  • Published : 1984.10.20
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Abstract

Reaction of acid chlorides with primary alcohols, secondary alcohols, and aryl alcohols in the presence of a catalytic amount of zinc chloride gave the corresponding esters in high yields, whereas the reaction with tertiary alcohols failed to give the esters due to the fast solvolytic reactions of tertiary alcohols with hydrogen chloride generated from the reaction. The use of molecular sieves as a scavenger for hydrogen chloride was found to be moderately effective in the reaction of mesitoyl chloride with tertiary alcohols. Reaction of acid chlorides with thiols in the presence of zinc chloride in acetonitrile proceeded cleanly, yielding the corresponding thiol esters in high yields.

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