Journal of Oleo Science
Online ISSN : 1347-3352
Print ISSN : 1345-8957
ISSN-L : 1345-8957
Chemistry and Organic Synthesis
Simple and Convenient Synthesis of Esters from Carboxylic Acids and Alkyl Halides Using Tetrabutylammonium Fluoride
Kouichi MatsumotoHayato ShimazakiYu MiyamotoKazuaki ShimadaFumi HagaYuki YamadaHirotsugu MiyazawaKeiji NishiwakiShigenori Kashimura
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2014 Volume 63 Issue 5 Pages 539-544


A simple and convenient method has been developed for the synthesis of esters from the corresponding carboxylic acids and alkyl halides by using a stoichiometric amount of tetrabutylammonium fluoride (Bu4NF) as the base. The reaction of carboxylic acids and a Bu4NF/THF solution in DMF or THF as the solvent generates carboxylate ions in situ. The carboxylate ions thus generated and accumulated are highly reactive. They are then allowed to react with alkyl halides as the electrophiles, and afford the corresponding esters in moderate to good yields. The reaction without Bu4NF does not afford any product; therefore, Bu4NF seems to play an important role as the base in these reactions. A bulky countercation such as the tetrabutylammonium cation seems to increase the reactivity of the carboxylate ions in the solution phase.

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© 2014 by Japan Oil Chemists' Society
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