4-Toluenesulfonyl chloride → p-Toluenesulfonic acid

Participants

Reaction Conditions

Reaction Steps

To a stirred suspension of p-toluenesulfonyl chloride (9.82 g, 51.5 mmol) in 2-{2-[2-(2-hydroxy-ethoxy)-ethoxy]-ethoxy}-ethanol, (20 g, 103 mmol) at 0° C. was added dropwise triethylamine (13 ml, 93 mmol). The suspension was stirred at 0° C. for 1 hour and then at room temperature for another 16 hours. The resulting mixture was dissolved in dichloromethane (350 ml). The clear and colourless solution that was obtained was extracted with 1 M hydrochloric acid (2×100 ml) and once with water (200 ml). The organic phase was dried (MgSO4), filtered and evaporated to afford a colourless oil. The crude product was purified by flash chromatography using ethyl acetate. Tetraethylene glycol ditosylate, eluted first followed by toluene-4Sulfonic acid 2-{2-[2-(2-hydroxy-ethoxy)ethoxy]-ethoxy}-ethyl ester, as a colourless oil; 8.89 g (49%).

Provenance & Evidence