4-Toluenesulfonyl chloride → 3-Hydroxypropyl 4-methylbenzenesulfonate

Participants

Reaction Steps

In 100 ml of triethylamine was dissovled 76 g (1.0 mole) of 1,3-propanediol, and 95 g (0.50 mole) of tosyl chloride was added to the solution, followed by stirring at room temperature overnight. The reaction mixture was concentrated under reduced pressure, and 800 ml of dichloromethane was added to the residue. The resulting mixture was washed with 150 ml of water, 120 ml of 1N hydrochloric acid and 150 ml of water, successively, and dried over anhydrous magnesium sulfate. The desiccating agent was filtered off and the filtrate was concentrated under reduced pressure. The residue was subjected to column chromatography of silica gel (600 g), and eluted with dichloromethane-methanol (96:4). The desired fracticns were concentrated under reduced pressure to give 1,3-propanediol monotosylate as a colorless oily material. Yield 86.9 g (yield: 78%).

Provenance & Evidence