Tetraethylene glycol di-p-tosylate

112-60-7

98-59-9

37860-51-8

77544-60-6

20.0 g of tetraethylene glycol triacetonitrile and 10.2 g of triethylamine were added to a reaction flask, 300 mL of acetonitrile was added to dissolve the mixture, and the mixture was cooled to 0-5°C in an ice bath. 19.0 g of p-toluenesulfonyl chloride was dissolved in 100 mL of acetonitrile and slowly added dropwise to the reaction mixture, the dropwise addition time was controlled at 1 hour. After the dropwise addition was completed, the temperature of the reaction mixture was raised to 20-25 °C and the reaction was continued for 12 hours. After completion of the reaction, the solvent was removed by rotary evaporation. The crude product was separated by column chromatography using gradient elution with hexane:ethyl acetate (v/v=4:1) and hexane:ethyl acetate (v/v=1.5:1). In the eluate of hexane:ethyl acetate (v/v=4:1), 12.9 g of oily product (tetraethylene glycol di-p-toluenesulfonate) was obtained in 35.9% yield. In the eluate of hexane:ethyl acetate (v/v=1.5:1), 5.4 g of oily product (tetraethyleneglycol mono-p-toluenesulfonate) was obtained in 10.4% yield.