Nitric Acid → Idramantone

Participants

Reaction Conditions

Reaction Steps

To a mixture of H2SO4 (96%; 150 ml) and HNO3 (70%; 15 ml), cooled to 0° C. is added tricyclo[3.3.1.13,7 ]decan-2-one (10 g; 0.067 mole) and the mixture stirred at room temperature for 5 hrs. The reaction mixture is then poured over ice, basified to pH 8 using 50% NaOH, extracted into ether, dried over MgSO4 and evaporated to dryness. The resultant product is recrystallized from carbon tetrachloride to obtain 5-hydroxytricyclo[3.3.1.13,7 ]decan-2-one [(m.p. 314° C. (dec.)] which is used directly in step B.

Provenance & Evidence