4-Toluenesulfonyl chloride → 2-(2-Hydroxyethoxy)ethyl 4-methylbenzenesulfonate

Participants

Reaction Steps

To a solution of diethylene glycol (22 g, 207.5 mmol) in CH2Cl2 (100 ml) was added triethylamine (10.5 g, 103.75 mmol). 9.89 (51.8 mmol) Toluene-4-sulfonyl chloride was added in one portion. The solution was stirred at room temperature for 1 hour. TLC was performed in 5% MeOH in DCM. After ½ hour a TLC showed formation of product. After 1 hour and 15 minutes the reaction mixture was washed with 0.1 M KHSO3 and 5% NaHCO3. The organic phase was dried with Na2SO3 and evaporated under reduced pressure. The crude reaction mixture was trapped on silica and purified by flash chromatography on a CombiFlash companion instrument (330 g column) using Hexane/EtOAc 50/50. Structure confirmed NMR.

Provenance & Evidence