Water → 2-(2-(2-Methoxyethoxy)ethoxy)ethyl 4-methylbenzenesulfonate

Participants

Reaction Conditions

Reaction Steps

A solution of triethylene glycol monomethyl ether (300 g) in tetrahydrofuran (550 mL) was added dropwise over 105 minutes to a stirred aqueous sodium hydroxide solution (2M, 1.28 L) at 0–5° C. A solution of p toluenesulphonyl chloride (383 g) in tetrahydrofuran (600 mL) was then added to the reaction mixture over 150 minutes, maintaining the temperature at 0–9° C. The reaction mixture was stirred at 0–5° C. for a further 2 hours and then allowed to warm to 20° C. and stirred for 16 hours. Additional aqueous sodium hydroxide solution (2M, 90 mL) was then added slowly to the reaction mixture and stirring was continued for a further 1 hour. Water (1 L) was added to the reaction mixture which was then extracted with toluene (2×1.8 L). The combined organic extracts were washed with water (3×1.8 L) and then concentrated in vacuo to give the title compound as a colourless oil (448 g). GC retention time 11.2 mins

Provenance & Evidence