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ChemicalBook CAS DataBase List 2-(2-(2-Methoxyethoxy)ethoxy)ethyl 4-Methylbenzenesulfonate
62921-74-8

2-(2-(2-Methoxyethoxy)ethoxy)ethyl 4-Methylbenzenesulfonate synthesis

9synthesis methods
-

Yield:62921-74-8 99%

Reaction Conditions:

with sodium hydroxide in tetrahydrofuran;water at 0; for 3 h;

Steps:

Toluene-4-sulfonic acid 2-[2-(2-methoxy-ethoxy)-ethoxy]-ethyl ester (1) (10a)

Sodium hydroxide (3.65 g, 91.3 mmol) and tri(ethyleneglycol) monomethyl ether (10.0 g, 60.9 mmol) weredissolved in a mixture of THF (140 mL) and water (20 mL).The solution was cooled in an ice bath. A solution of p-toluenesulfonyl chloride (12.76 g, 67.0 mmol) in THF (20 mL)was added slowly. The solution was stirred at 0 °C for 3 hand then poured into ice water (50 mL). The mixture wasextracted several times with methylene chloride. The combinedorganic layer was washed with dilute HCl and brineand then dried over MgSO4. After filtration, the solvent wasremoved under reduced pressure to afford the productas colourless oil. Yield 19.23 g (99%). 1H NMR (400 MHz,CDCl3): δ 2.42 (s, 3H), 3.35 (s, 3H), 3.50 (t, 2H), 3.59 (q, 6H),3.67 (t, 2H), 4.14 (t, 2H), 7.32 (d, 2H) , 7.78 (d, 2H).

References:

Jung, Su Hee;Lee, Ji-Won;Kim, Hee-Joon [Supramolecular Chemistry,2016,vol. 28,# 7-8,p. 634 - 639]

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