Acetone → 2,4-Dimethoxy-4b,5,6,8,8a-hexahydro-9(10H)-phenanthrone

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Reaction Steps

To a flask equipped with a stirrer, dropping funnel, condenser, and gas inlet tube maintained under a nitrogen atmosphere, there is added 23.2 g. (0.1 mole) of 2,4-dihydroxy-4b,5,6,7,8,8a,9,10-octahydro-9-oxo-phenanthrene, 20 g. (0.15 mole) of dimethyl sulfate, 22 g. (0.16 mole) of dry potassium carbonate and 500 ml. of dry acetone, the resulting mixture is then refluxed with stirring overnight. The resulting suspension is cooled, 5 ml. of water is added and stirring is continued for an additional 5 minutes. The mixture is filtered, and the filtrate is concentrated to dryness. The resulting residue is recrystallized from acetone/methanol to give 2,4-dimethoxy-4b,5,6,7,8,8a,9,10-octahydro-9-oxo-phenanthrene; m.p. 130°-131° C.

Provenance & Evidence