Issue 39, 2022

Efficient and practical synthesis of monoalkyl oxalates under green conditions

Abstract

Monoalkyl oxalates are among the most important building blocks being applied to the synthesis of a variety of significant classes of compounds or applied to various cutting-edge reactions. However, their commercial availability is limited. Their synthetic methods are also limited because of the difficulty to synthesize them, and those hitherto reported are carried out in organic solvents often with the use of toxic reagents with mostly low to modest yields. Here we have developed practical synthesis of monoalkyl oxalates in aqueous media by applying the highly efficient selective monohydrolysis reactions of symmetric diesters which we reported previously. The best conditions apply an aqueous NaOH solution with relatively nontoxic THF or acetonitrile as a co-solvent at around 0–5 °C. The procedures are simple and environmentally friendly without requiring toxic or expensive reagents, yet yielding the corresponding half-esters in high yields with high purities. All the half-esters prepared here are stable over a long period of time. Therefore, our studies are expected to offer practical green methods for the synthesis of monoalkyl oxalates.

Graphical abstract: Efficient and practical synthesis of monoalkyl oxalates under green conditions

Supplementary files

Article information

Article type
Paper
Submitted
17 7 2022
Accepted
23 8 2022
First published
12 9 2022
This article is Open Access
Creative Commons BY license

RSC Adv., 2022,12, 25669-25674

Efficient and practical synthesis of monoalkyl oxalates under green conditions

T. Barsukova, T. Sato, H. Takumi and S. Niwayama, RSC Adv., 2022, 12, 25669 DOI: 10.1039/D2RA04419F

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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