Reacción #331480

Ecuación de reacción

NaHSO3

Florisil

compound

4,5-dibromo-1-cyclohexene

N-methylmorpholine

→

4,5-dibromo-1,2-cyclohexanediol

Disolventes

water

water

acetone

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGwas vigorously stirred for 24 hours
2. 2
   OtroAfter the completion of the reaction
3. 3
   workup.ADDITIONwas added to the reaction solution
4. 4
   workup.STIRRINGwas stirred for 10 minutes
5. 5
   OtroAfter that, insoluble matter was removed by celite filtration, and 5% HCl
6. 6
   workup.ADDITIONwas added to the filtrate until the pH of the filtrate
7. 7
   Otrowas removed under reduced pressure
8. 8
   ExtracciónOrganic matter was extracted from the remainder with ethyl acetate
9. 9
   Secadodried over sodium sulfate
10. 10
    Concentraciónconcentrated under reduced pressure
11. 11
    FiltraciónThe precipitated crystals were filtrated
12. 12
    Otrowas then recrystallized with methylene chloride

Procedimiento

The compound obtained in Step (9) (80.5 g, 338 mmol), water (500 ml), acetone (250 ml), and N-methylmorpholine (45.5 g, 389 mmol) were placed in a reaction vessel, and was stirred. OsO4 (1 g) was added to the mixture, and was vigorously stirred for 24 hours. After the completion of the reaction, a suspension of NaHSO3 (50 g) and Florisil (250 g) in water (100 ml) was added to the reaction solution, and was stirred for 10 minutes. After that, insoluble matter was removed by celite filtration, and 5% HCl was added to the filtrate until the pH of the filtrate became 3. Upon confirming that the pH had reached 3, and acetone was removed under reduced pressure. Organic matter was extracted from the remainder with ethyl acetate, dried over sodium sulfate, and concentrated under reduced pressure. The precipitated crystals were filtrated, and was then recrystallized with methylene chloride, whereby 4,5-dibromo-1,2-cyclohexanediol was obtained (64.6 g, 70%).

Fuente