Hydrochloric Acid → Octahydro-4,7-methano-1H-inden-5-ol

25 g of tricyclo[5.2.1.0 (2,6)]decan-8-one (Aldrich) were dissolved in 100 ml of methanol and, at room temperature and with slight cooling and stirring, admixed a little at a time with 6.3 g of solid sodium borohydride over a period of 2 h. The mixture was then stirred for another 2 h and allowed to stand overnight. With cooling, about 40 ml of 2 N HCl were then added dropwise, followed by 20 ml of water. The mixture was concentrated, the residue was admixed with ethyl acetate, and the ethyl acetate phase was washed once with water and once with sodium bicarbonate solution. The ethyl acetate phase was dried using magnesium sulfate and then filtered and concentrated. This gave 26 g of an oil which was purified by distillation under reduced pressure. This gave 20.7 g of an oily liquid (bp0.5 76° C.).

1. temperaturewith slight cooling
2. customof 2 h
3. stirringThe mixture was then stirred for another 2 h
4. temperatureWith cooling
5. concentrationThe mixture was concentrated
6. washthe ethyl acetate phase was washed once with water and once with sodium bicarbonate solution
7. dry with materialThe ethyl acetate phase was dried
8. filtrationfiltered
9. concentrationconcentrated
10. distillationThis gave 26 g of an oil which was purified by distillation under reduced pressure
11. customThis gave 20.7 g of an oily liquid (bp0.5 76° C.)

ORD record

ord-8173ae6be2ab4d44a87a0d8a4d585d49

Source dataset

uspto-grants-2004_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06825231B2