NOTES 3013After separating and drying the crude product, it was dissolved in benzene-60' naphtha solution and decolorized twice with Norite. and the solution evauorated to dnmess an equivalent amount of roll sulfur was carried out using the above procedure giving 0.3 g. of XVII identical with that obtained from XV. in vacuo. The residue was recrystallized from absolute Anal. alcohol-acetone solution to give 0.2 g. of XVII, m.p. 115.2-11.5 80 for C22~ls02: C, a . 0 7 ; H, 5.73. Found: c, 84.24; H, 6.02. _--.-. b. From XI1.-Dehydrogenation of 0.7 g. of XI1 with MISSOULA, MONTANA Synthesis of Phenanthrenes. VI. 5-Hydroxy-8-(5) The experimental verification of this prediction is currently in progress. (6) J. W. Cornforth and R. Robinson, J . Ckem. Soc.. 1855 (1949). 204" (capillary). The analytical sample prepared by furthe: recrystallization from benzene melted at 200.1-200.7 (hot stage). Anal. Calcd. for C~~H Z O O~: C, 77.55; H , 8.68. Found: C, 77.45; H, 8.70. The ultraviolet spectral curve of I1 in ethanol had two maxima, one at 295 m p (log E 3.55), the other at ca. 225 mp could not be determhed accurately with our instrument.An attempt to purify I1 by dissolving in aqueous alkali led to the formation of a brown tar from which a yellow solid could be isolated. An oxidation of I1 (0.93 g.) according to the procedure of Smith and Irwins yielded 0.51 g. (55%) of crude quitlone, m.p. 53-58'.Sublimation produced golden yellow crystals which melted a t 60-62". This quinone was extremely sensitive to air oxidation and darkened rapidly on standin . The ultraviolet spectral curve had maxima at 250 mp bog e 3.85) and 295 mp (log E 3.45) 5 ,&Diacetoxy4a-methyl-1,2,3,4,4a ,9,10,10a-octahyd~ophenanthrene.-A mixture of I1 (0.6 g.), acetic anhydride (2.7 g.) and pyridine ( 5 ml.) was allowed to stand a t room temperature for 40 hours. The reaction mixture was poured into ice-water containing hydrochloric acid (5 nil.) and the product extracted with ether. Evaporation of the ether left a crystalline product (0.5 g., 61%) which melted a t 87-93". The analytical sample was prepared by alternate recrystallization from methanol and ethyl ether-petroleum ether, m.p. 93.594.2'.Anal. Calcd. for C,sH?rOa: C, 72.13; H , 7.65. Found: C, 72.09; H, 7.73.Hydrogenation of II. A.-A solution of I1 (2.1 9.) in dioxane (50 ml.) was hydrogenated for four hours at 2800 p . s i . and 170-185" using palladium-on-strontium carbonate (2.1 8.) as a catalyst. The catalyst was filtered from the solution and the solvents removed to leave a brown solid residue. Recrystallization of this substance from benzene yielded three crops of unchanged hydroquinone I1 (0.57 g.) in various stages of purity. The filtrate from these cry\tallizations was separated by chromatographic fractionation to yield two major components: (1) quinone, m.p. 52-87' formed by air oxidation of I1 during processing and (2) an isomer bf 5,8dihydroxy-4a-methylperhydrophenanthrene, IVa (0.12 g.) which melted at 193.5-195" after recrystallization from acetone.Anal. Calcd. for CI6H26O1: C, 7...