4-Toluenesulfonyl chloride → Tetraethylene glycol p-toluenesulfonate

Temperature

0 °C

Into a 250-mL round-bottom flask was placed a solution of tetraethylene glycol (50 g, 257.47 mmol, 9.81 equiv) in DCM (150 mL) and triethylamine (8 g, 79.05 mmol, 3.01 equiv). This was followed by the addition of a solution of 4-methylbenzene-1-sulfonyl chloride (5.0 g, 26.23 mmol, 1.00 equiv) in DCM (10 mL) dropwise with stirring at 0° C. The resulting solution was stirred for 2 h at room temperature, at which time it was diluted with 200 ml of hydrogen chloride (3N aq.). The resulting solution was extracted with 2×150 mL of DCM and the combined organic layers were washed with 3×150 mL of saturated sodium bicarbonate. The mixture was dried over sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:5˜ethyl acetate). This resulted in 7.0 g (77%) of 2-(2-(2-(2-hydroxyethoxy)ethoxy)ethoxy)ethyl 4-methylbenzenesulfonate as colorless oil.

1. customInto a 250-mL round-bottom flask was placed
2. stirringThe resulting solution was stirred for 2 h at room temperature, at which time it
3. extractionThe resulting solution was extracted with 2×150 mL of DCM
4. washthe combined organic layers were washed with 3×150 mL of saturated sodium bicarbonate
5. dry with materialThe mixture was dried over sodium sulfate
6. concentrationconcentrated under vacuum
7. customThis resulted in 7.0 g (77%) of 2-(2-(2-(2-hydroxyethoxy)ethoxy)ethoxy)ethyl 4-methylbenzenesulfonate as colorless oil

ORD record

ord-37d20df6da15420eab667eb60669f53f

Source dataset

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09408840B2