4-Toluenesulfonyl chloride → 3-Hydroxypropyl 4-methylbenzenesulfonate

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%).

1. additionwas added to the solution
2. concentrationThe reaction mixture was concentrated under reduced pressure, and 800 ml of dichloromethane
3. additionwas added to the residue
4. washThe resulting mixture was washed with 150 ml of water, 120 ml of 1N hydrochloric acid and 150 ml of water
5. dry with materialsuccessively, and dried over anhydrous magnesium sulfate
6. filtrationThe desiccating agent was filtered off
7. concentrationthe filtrate was concentrated under reduced pressure
8. washeluted with dichloromethane-methanol (96:4)
9. concentrationThe desired fracticns were concentrated under reduced pressure

ORD record

ord-6996f856815744c6b08d4452a2f5940e

Source dataset

uspto-grants-1987_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04710579