Tosylation transforms the stable alcoholic group into a fragile leaving group of sulfonic ester/tosylate. Tosylate is the hub for a variety of functional group interconversion hence it has a huge impact on natural products and pharmaceuticals. Tosyl group also plays an important role in oligonucleotide chemistry and amino acid chemistry. Glycols up to six ethylene glycol units and diols up to decane units were tosylates under controlled and mild conditions. The complete consumption of tosyl chloride was monitored by TLC then the reaction mixture was extracted to remove excess glycols or diols and pyridinium salt. The majority of ditosylated bi-product and remaining pyridine were removed by precipitation. Tosylated derivatives of glycol and diols were synthesized with a higher overall yield. Products were analyzed with TLC and ESI and NMR. The product does not require any expensive flash column chromatographic separation.

Chromatography free synthesis of mono tosylate derivatives of glycols and diols

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ACS Fall 2022

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