cis-1,2,3,6-Tetrahydrophthalimide → 3-(cis-1,2,3,6-Tetrahydrophthalimido)-1-propanol

Temperature

0 °C

15.1 g. of cis-1,2,3,6-tetrahydrophthalimide are dissolved in 15 ml of methanol in which has previously been dissolved, 2.3 g of sodium metal. The mixture is evaporated to dryness under reduced pressure. 14 g. of 3-bromo-1-propanol are added to the solid, warming occurs. When the heating subsides, 40 ml of dimethylformamide are added with heating under reflux for 6 hours. After cooling, 200 ml of water and 100 ml of methylene chloride are added. The mixture is shaken and the aqueous phase discarded. The organic extract is washed with water (2×50 ml) and the methylene chloride solution is dried over anhydrous sodium sulfate. The solution is concentrated to about 50 ml and hexane added near the cloud point. Cooling to 0° C. precipitates 3-(cis-1,2,3,6-tetrahydrophthalimido)-1-propanol (1b).

1. dissolutionhas previously been dissolved
2. customThe mixture is evaporated to dryness under reduced pressure
3. additionof 3-bromo-1-propanol are added to the solid
4. temperaturewarming
5. additionWhen the heating subsides, 40 ml of dimethylformamide are added
6. temperaturewith heating
7. temperatureunder reflux for 6 hours
8. temperatureAfter cooling
9. addition200 ml of water and 100 ml of methylene chloride are added
10. extractionThe organic extract
11. washis washed with water (2×50 ml)
12. dry with materialthe methylene chloride solution is dried over anhydrous sodium sulfate
13. concentrationThe solution is concentrated to about 50 ml and hexane
14. additionadded near the cloud point
15. customprecipitates 3-(cis-1,2,3,6-tetrahydrophthalimido)-1-propanol (1b)

ORD record

ord-7f258fd6c04e4d028f3fc5d0855a2d8e

Source dataset

uspto-grants-1995_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05411869