1,2-Bis(tosyloxy)ethane

107-21-1

98-59-9

6315-52-2

The general procedure for the synthesis of 1,2-bis(tolyloxy)ethane from ethylene glycol and p-toluenesulfonyl chloride was as follows: 19.8 g (0.3 mol) of ethylene glycol was dissolved in 150 mL of distilled pyridine, and the solution was subsequently cooled in an ice bath. Under mechanical stirring, p-toluenesulfonyl chloride (123 g, 0.65 mol) was slowly added and it was ensured that the reaction temperature was maintained below 20°C during the addition. When approximately 90 g of p-toluenesulfonyl chloride was added, stirring was difficult due to the increased viscosity of the mixture, at which point 200 mL of pyridine was added for dilution. Stirring of the reaction mixture was continued for 2 hours and 30 minutes. Upon completion of the reaction, an aqueous HCl solution consisting of 12 N HCl (170 mL) and ice (500 mL) was added to the mixture. The solid formed in the process was removed by filtration. The resulting solid was dissolved in 250 mL of refluxing methanol and subsequently filtered to remove the newly formed precipitate after cooling to room temperature. Finally, the obtained white solid was dried under vacuum to give the pure product 1,2-bis-toluoxyethane (92.4 g, 83% yield). The product was characterized as follows: 1H NMR (200 MHz, CDCl3) δ 7.71 (d, 2H), 7.31 (d, 2H), 4.16 (s, 2H), 2.43 (s, 3H).