Pyridine → 3-Methoxypropyl 4-methylbenzenesulfonate

Participants

Reaction Steps

4-Methyl-benzenesulfonyl chloride (21 g, 110.0 mmol, 1.1 equiv.) was added at 0° C. to a solution of 3-methoxy-propan-1-ol (9 g, 100.0 mmol, 1.0 equiv.) in pyridine (16.1 ml, 200.0 mmol, 2.0 equiv.). After 1 hr at 0° C. a white solid was formed. It was diluted with water and extracted twice with ethyl acetate. The combined organics were washed with KHSO4/K2SO4 and brine, dried over Na2SO4, filtered, evaporated and crystallized from ether (hygroscopic) to give toluene-4-sulfonic acid 3-methoxy-propyl ester, 21.4 g, m/e 245.0 (MH+).

Provenance & Evidence