Al₂O₃/MeSO₃H (AMA) as a new reagent with high selective ability for monoesterification of diols

Hashem Sharghi* and Mona Hosseini Sarvari

*Department of Chemistry, Faculty of Science, Shiraz University, Shiraz 71454, Iran, Email: shashemchem.susc.ac.ir

H. Sharghi, M. Hosseini Sarvari, Tetrahedron, 2003, 59, 3627-3633.

DOI: 10.1016/S0040-4020(03)00518-0

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Abstract

A new facile method for selective monoesterification of diols - in particular oligoethylene glycols - has been developed. The reaction of diols with aromatic and aliphatic acids in presence of Al₂O₃ and MeSO₃H gave monoesterified products in excellent yields without use of any solvents.

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Details

The document discusses a new method for the selective monoesterification of diols using a reagent mixture of Al₂O₃ and methanesulfonic acid (MeSO₃H), referred to as AMA. This method, developed by Hashem Sharghi and Mona Hosseini Sarvari from Shiraz University, offers high selectivity and excellent yields without the need for solvents. The process is particularly effective for oligoethylene glycols and various aromatic and aliphatic acids, achieving monoesterification in a short reaction time at 80°C. The method addresses the common issue of diester formation in diol esterification, simplifying the separation process. Compared to traditional methods using dibutyltin oxide or microwave irradiation, AMA is more efficient, cost-effective, and easier to purify. The study highlights the versatility of AMA in organic synthesis, including its application to other 1,n-diols and amino alcohols, and its potential for industrial use due to its simplicity, high yields, and lack of solvent requirement. The research findings are supported by detailed experimental procedures and characterization data for the synthesized monoesters.

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Key Words

monoesterification, benzoic acid, Fischer esterifcation

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ID: J72-Y2003-350