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

Mechanism

Original Paper

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