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Aqueous sodium tosylate: a sustainable medium for alkylations
Green Chemistry ( IF 9.3 ) Pub Date : 2024-02-13 , DOI: 10.1039/d3gc04206e
Sem Bleus 1 , Jeltzlin Semerel 1, 2 , Wim Dehaen 1
Affiliation  

Typical alkylation reactions produce significant amounts of undesired salt and solvent waste. Herein, we report an efficient alkylation protocol utilising aqueous sodium tosylate (NaTos) solutions as a hydrotrope-containing medium. The methodology represents an inexpensive and straightforward approach for preparing alkyl aryl ethers, thioethers and N-alkylated tosyl amides in high yields under mild conditions. The generated reaction waste, aqueous NaTos salt, was repurposed as a reaction medium in subsequent steps. This medium was recycled ten times without any significant change in the yield, providing an improved environmental factor over various literature examples. Under similar conditions, commonly applied solvents furnished the products with lower yields and more waste.

中文翻译:

甲苯磺酸钠水溶液:可持续的烷基化介质

典型的烷基化反应会产生大量不需要的盐和溶剂废物。在此,我们报告了一种利用甲苯磺酸钠 (NaTos) 水溶液作为含有水溶助长剂的介质的有效烷基化方案。该方法代表了一种在温和条件下以高产率制备烷基芳基醚、硫醚和N-烷基化甲苯磺酰胺的廉价且直接的方法。产生的反应废物,NaTos 盐水溶液,在后续步骤中被重新用作反应介质。该介质被回收十次,产量没有任何显着变化,与各种文献示例相比,提供了改进的环境因素。在类似的条件下,常用的溶剂使产品的产率较低且浪费较多。
更新日期:2024-02-13
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