Water → Azacyclonol

Participants

Reaction Conditions

Reaction Steps

A 1.4 L hydrogenation shaker bomb was charged with 43.00 grams (0.165 moles) diphenyl-4-pyridylcarbinol, 8.00 grams 50% H2O wet 5% Pd on carbon (4 grams dry) and 350 ml xylene. The bomb was sealed, pressurized with 900 psi H2, and heated with shaking to 170° C. After 17 hours, the pressure was 1075 psi (at 170° C.) and the bomb was allowed to cool. The contents are poured out, heated to 70° C. and suction filtered carefully to remove the catalyst. GC analysis of the filtrate and washes at this point indicated 6.9% azacyclonol and 0.05% diphenyl-4-pyridylcarbinol. The filtrate was topped off on a rotary evaporator to a constant weight (42.65 grams). The sticky crude azacyclonol was removed and recrystallized from 200 ml heptane and 165 ml xylene. After chilling, filtration and over drying (2 hours, 100° C., 15 mm) a yield of 37.84 grams or 86.0% of azacyclonol was obtained, having a melting point of 163°-166° C.

Provenance & Evidence