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

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Reaction Steps

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.).

Provenance & Evidence