Acetic Acid → 2,4-Dihydroxy-4b,6,7,8,8a,10-hexahydrophenanthren-9(5H)-one

Participants

Reaction Conditions

Reaction Steps

To a flask equipped with a stirrer, dropping funnel, condenser and gas inlet tube maintained under a nitrogen atmosphere, there is added 50 g (0.89) moles of potassium hydroxide in one liter of 2-methoxyethanol. Stirring is initiated and 100 g(0.79mole) of anhydrous phloroglucinol is added in three portions, followed by the addition of 100 g (0.80 mole) of 1-acetyl-cyclohexene while maintaining the temperature at 50°C. The resulting solution is refluxed at 140°C for 4 hours. After cooling there is then added gradually 53.6 g. of acetic acid while obtaining a pH of approximately 7. The solvent is then removed in vacuo, and the residue is further heated in vacuo in a bath at 70°C, to obtain a viscous residue. The resulting residue is dissolved in ethyl acetate and water; washed twice with water, dried over anhydrous sodium sulfate, filtered and evaporated in vacuo to obtain a brown solid. The resulting solid is recrystallized from ethyl acetate/cyclohexane to give 2,4-dihydroxy-4b,5,6,7,8,8a,9,10-octahydro-9 -oxo-phenanthrene. m.p. 220°-223°C.

Provenance & Evidence