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image of Improved Process for Esterification Reaction of Carboxylic Acid using N-Bromosuccinimide and Triphenylphosphine as Activating Agents

Abstract

Background

The ester functional group is crucial in organic chemistry as well as in other fields due to its diverse applications. Thus, its synthesis in a simple and effective manner remains an interesting task. In literature, many one-pot reactions are reported for the transformation of carboxylic acid into ester. However, many of them are inapplicable due to their limitations, such as, longer reaction time, harsh reaction conditions, usage of expensive reagents, etc. Hence, a simple as well as effective transformation of carboxylic acid to ester is still desirable.

Objective

The study intends to develop a procedure for esterification reaction in a simple and cost effective manner under a mild reaction condition.

Methods

The demonstration reflects the activation of carboxylic acid employing a combination of triphenylphosphine and N-bromosuccinimide (NBS) at low temperatures. The activated carboxylic acid reacts with alcohol to form the corresponding ester. At elevated temperatures, the reaction can be completed at a faster rate, while at room temperatures the process is relatively slower and takes quite a long time.

Results

Carboxylic acids (containing aromatic and heteroaromatic moieties) were made to react with different alcohols, and the desired esters were obtained quickly under optimum reaction conditions. Good to excellent yields of the desired esters were obtained in most of the reactions.

Conclusion

An ameliorated procedure for the esterification of carboxylic acid is reported. Activation of carboxylic acid was achieved using triphenylphosphine and NBS. The activated acid thus formed, upon reaction with various alcohols, produced the corresponding ester in good yields.

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2025-06-04
2025-09-03

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Improved Process for Esterification Reaction of Carboxylic Acid using N-Bromosuccinimide and Triphenylphosphine as Activating Agents
Bentham Science Publishers ; https://doi.org/10.2174/0122133372367716250526102311
/content/journals/cocat/10.2174/0122133372367716250526102311
/content/journals/cocat/10.2174/0122133372367716250526102311
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NMR spectra of all compounds are available in the supporting information file.

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  • Article Type:     Research Article
Keywords: ethyl ester ; methyl ester ; allyl ester ; carboxylic acid ; Efficient conversion ; N-bromosuccinimide ; triphenylphosphine

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