Exploring Controlled Synthesis for Green Production of Mono-tosylates from Diols and Glycols in Undergraduate Research

Tosylation involves the conversion of a stable alcohol group into a delicate leaving group, specifically a sulfonic ester or tosylate. Tosylate serves as a central element in numerous functional group conversions, exerting a significant influence on the realms of natural products and pharmaceuticals. Additionally, the Tosyl group holds notable importance in oligonucleotide and amino acid chemistry. The conventional synthesis of mono-tosylates from glycols and diols is fraught with challenges, being inherently difficult, time-consuming, and yielding minimal output. Compounding these issues is the considerable expense associated with the purification process. In this study, we present an innovative, environmentally friendly, and controlled synthetic approach for generating mono-tosylates with enhanced yields. The resulting product is meticulously characterized using TLC and LC-MS methods. An exceptional aspect of this project lies in its execution by undergraduate researchers, where the adoption of a green synthesis approach not only accelerates the process by eliminating the need for flash columns but also enhances efficiency and simplifies operational procedures. Consequently, this methodology holds promise for consideration in undergraduate organic laboratories and projects.