Water → Tetraethylene glycol p-toluenesulfonate

Participants

Reaction Steps

A cold (0°) solution of 23.3 g of tetraethylene glycol and 19 g of pyridine in 100 ml of methylene chloride, is treated portionwise while stirring vigorously with a total of 19 g of p-toluenesulphonyl chloride. After completion of the addition the mixture is stirred at room temperature for a further 5 hours. 200 ml of methylene chloride and 100 ml of water are then added thereto and the organic phase is separated. The organic phase is washed successively with 100 ml of 2N hydrochloric acid, 100 ml of 5% sodium hydrogen carbonate solution and 100 ml of water and dried over sodium sulphate. The solvent is removed in a vacuum and the residue is chromatographed over 400 g of silica gel with methylene chloride-ethyl acetate-methanol (5:4:1) as the eluent. In addition to small amounts of tetraethylene glycol ditosylate there are isolated 17 g of tetraethylene glycol monotosylate as a colourless liquid. RF (silica gel/methylene chloride-ethyl acetate-methanol 5:4:1): 0.6.

Provenance & Evidence