Phenanthrene picrate

Solubility of Phenanthrene Picrate in Alcoholic Solutions Containing Picric Acid and also Phenanthrene. 

Methyl-1,2-cyclopentenophenanthrene (16,17-dihydro-17-methyl-15ff-cyclopenta-[a] -phenanthrene [549-38-2] M 232.3, m 126-127 . Crystallise it from AcOH or EtOH (plates, m 125.5-126°). The picrate has m 130-131 (orange-red needles from EtOH). [Tatta Bardhan J Chem Soc (C) 893 1968, Beilstein 5 IV 2433.]... 

The AT-methylanonaine was obtainable by reaction with forniic acid and formaldehyde, and Hofmann degradation via A-methylanonaine methiodide (m.p. 217°) gave a methine base (m.p. 87-90°) and a vinyl-phenanthrene (m.p. 87°) which on oxidation generated a phenanthrene-carboxylic acid (m.p. 240°) which could be decarboxylated to what was evidently 3,4-methylenedioxyphenanthrene (m.p. of picrate, 168°). 

Octahydrophenanthrene (4.0 g) was heated with 4.0 g 10% palladized charcoal at 210-270°C for 3 h in a slow steam of carbon dioxide. The mass was cooled and thoroughly extracted with ether. The solvent was removed, and 3.5 g crude phenanthrene was purified through its picrate, affording 3.0 g phenanthrene, m.p., 100°C. 

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