Aluminum isopropoxide → Zearalanol

Temperature

75 °C

Aluminum isopropoxide (300 g, 1.4688 moles) is added to a solution of Zearalenone (100 g, 0.3141 moles) in 1000 g (1270 mL) of 2-propanol. The mixture is stirred at 75° C. for 24 hours then the mixture is distilled to a volume of about 500 mL, cooled to ambient room temperature, 400 mL of water and 550 mL of 6N HCl are added ensuring that the reaction temperature is maintained below 40° C. The reaction is cooled to ambient room temperature and 886 g (990 mL) of ethyl acetate is added. The aqueous layer is separated and the ethyl acetate layer is extracted 2×325 mL with water and 1×325 mL with brine. The ethyl acetate is replaced with methanol by distilling off the ethyl acetate and replacing it with 380 g (480 mL) of methanol. The methanol mixture is filtered to remove insoluble matter and 10% Palladium on carbon (10 g) is added followed by hydrogen (1 atmosphere of pressure) at ambient room temperature. The reaction is stirred for 8 hours then Celite (20 g) is added and the reaction stirred for an additional hour. The reaction mixture is filtered to remove insoluble matter and water (725 mL) is added. The mixture is stirred at ambient room temperature for 4 hours during which time solid precipitate. The solids are isolated by filtration and washed with heptane (1000 mL). The solids are dissolved in methanol (890 mL) and water (470 mL) is added at ambient room temperature and solids begin to crystallize from solution. The mixture is stirred for an additional 4 hours and the solids are isolated by filtration, dried under vacuum to a moisture content of less than 0.5% to yield pure Zeranol (45.6 g, 45%).

1. distillationthe mixture is distilled to a volume of about 500 mL
2. temperaturecooled to ambient room temperature
3. addition400 mL of water and 550 mL of 6N HCl are added
4. temperatureis maintained below 40° C
5. temperatureThe reaction is cooled to ambient room temperature
6. addition886 g (990 mL) of ethyl acetate is added
7. customThe aqueous layer is separated
8. extractionthe ethyl acetate layer is extracted 2×325 mL with water and 1×325 mL with brine
9. distillationby distilling off the ethyl acetate
10. filtrationThe methanol mixture is filtered
11. customto remove insoluble matter and 10% Palladium on carbon (10 g)
12. additionis added
13. customfollowed by hydrogen (1 atmosphere of pressure) at ambient room temperature
14. stirringThe reaction is stirred for 8 hours
15. additionCelite (20 g) is added
16. stirringthe reaction stirred for an additional hour
17. filtrationThe reaction mixture is filtered
18. customto remove insoluble matter and water (725 mL)
19. additionis added
20. stirringThe mixture is stirred at ambient room temperature for 4 hours during which time solid precipitate
21. customThe solids are isolated by filtration
22. washwashed with heptane (1000 mL)
23. dissolutionThe solids are dissolved in methanol (890 mL)
24. additionwater (470 mL) is added at ambient room temperature
25. customto crystallize from solution
26. stirringThe mixture is stirred for an additional 4 hours
27. customthe solids are isolated by filtration
28. customdried under vacuum to a moisture content of less than 0.5%

ORD record

ord-b0e684b4db544e58b8d38e26a47a8f0b

Source dataset

uspto-grants-2014_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08674120B2