Water → (R)-3-hydroxybutyl 4-methylbenzenesulfonate

Temperature

-25 °C

After adding pyridine (100 ml) to (R)-1,3-butanediol (86.0 g), the solution was cooled to −25° C. under nitrogen atmosphere. A solution of p-toluenesulfonyl chloride (200 g) in pyridine (200 ml) was slowly added dropwise thereto at a temperature ranging from −20 to −10° C. The mixture was stirred for 1 hour at a temperature ranging from −20 to −10° C. A small amount of water was added to the reaction mixture to stop the reaction and the solution was extracted with toluene and water. The organic layer was washed with water, dried over sodium sulfate, and concentrated under reduced pressure to obtain (R)-3-hydroxy-1-(p-toluenesulfonyloxy)butane (209 g) as light brown oil. The oil thus obtained was used in the next step as such without purification.

1. customranging from −20 to −10° C
2. customranging from −20 to −10° C
3. customthe reaction
4. extractionthe solution was extracted with toluene and water
5. washThe organic layer was washed with water
6. dry with materialdried over sodium sulfate
7. concentrationconcentrated under reduced pressure

ORD record

ord-cdd6798588e847b2a5bc0fcbafb4822d

Source dataset

uspto-grants-2002_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06420409B1