The Yamaguchi esterification converts a carboxylic acid to an ester. First, triethylamine (Et3N) deprotonates the carboxylic acid, which then attacks the Yamaguchi reagent (2,4,6-trichlorobenzoyl chloride) to produce an acid anhydride. The Yamaguchi reagent is released when the acid anhydride is attacked by 4-dimethylaminopyridine (DMAP). The alcohol displaces DMAP and a final deprotonation yields the ester.

  • Reagents: Et3N, Yamaguchi Reagent (2,4,6-Trichlorobenzoyl Chloride), DMAP, Alcohol
  • Reactant: Carboxylic Acid
  • Product: Ester
  • Type of Reaction: Esterification (Acyl Substitution)
  • Bond Formation: O=C-O-R


Top Citations

Original Paper

Related Reactions

  • Fischer Esterification
  • Steglich Esterification
  • Synthesis of Esters

Related Compounds

  • Et3N (CAS 121-44-8)
  • Yamaguchi Reagent (CAS 4136-95-2)
  • DMAP
  • Alcohol
  • Carboxylic Acid
By shuhan yang


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