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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
- Investigation of the Yamaguchi Esterification Mechanism. Synthesis of a Lux-S Enzyme Inhibitor Using an Improved Esterification Method Org. Lett. 2006, 8 (1), 47–50.
- Modified Yamaguchi Reagent: Convenient and Efficient Esterification. Synthetic Communications 2014, 44 (19), 2854–2860.
- Fischer Esterification
- Steglich Esterification
- Synthesis of Esters
- Et3N (CAS 121-44-8)
- Yamaguchi Reagent (CAS 4136-95-2)
- Carboxylic Acid