Phenanthrene 2- cyclohexanone

AI3-00040, see Cyclohexanol AI3-00041, see Cyclohexanone AI3-00045, see Diacetone alcohol AI3-00046, see Isophorone AI3-00050, see 1,4-Dichlorobenzene AI3-00052, see Trichloroethylene AI3-00053, see 1,2-Dichlorobenzene AI3-00054, see Acrylonitrile AI3-00072, see Hydroquinone AI3-00075, see p-Chloro-rrr-cresol AI3-00078, see 2,4-Dichlorophenol AI3-00085, see 1-Naphthylamine AI3-00100, see Nitroethane AI3-00105, see Anthracene AI3-00109, see 2-Nitropropane AI3-00111, see Nitromethane AI3-00118, see ferf-Butylbenzene AI3-00119, see Butylbenzene AI3-00121, see sec-Butylbenzene AI3-00124, see 4-Aminobiphenyl AI3-00128, see Acenaphthene AI3-00134, see Pentachlorophenol AI3-00137, see 2-Methylphenol AI3-00140, see Benzidine AI3-00142, see 2,4,6-Trichlorophenol AI3-00150, see 4-Methylphenol AI3-00154, see 4,6-Dinitro-o-cresol AI3-00262, see Dimethyl phthalate AI3-00278, see Naphthalene AI3-00283, see Di-rj-butyl phthalate AI3-00327, see Acetonitrile AI3-00329, see Diethyl phthalate AI3-00399, see Tributyl phosphate AI3-00404, see Ethyl acetate AI3-00405, see 1-Butanol AI3-00406, see Butyl acetate AI3-00407, see Ethyl formate AI3-00408, see Methyl formate AI3-00409, see Methanol AI3-00520, see Tri-ocresyl phosphate AI3-00576, see Isoamyl acetate AI3-00633, see Hexachloroethane AI3-00635, see 4-Nitrobiphenyl AI3-00698, see IV-Nitrosodiphenylamine AI3-00710, see p-Phenylenediamine AI3-00749, see Phenyl ether AI3-00790, see Phenanthrene AI3-00808, see Benzene AI3-00867, see Chrysene AI3-00987, see Thiram AI3-01021, see 4-Chlorophenyl phenyl ether AI3-01055, see 1.4-Dioxane AI3-01171, see Furfuryl alcohol AI3-01229, see 4-Methyl-2-pentanone AI3-01230, see 2-Heptanone AI3-01231, see Morpholine AI3-01236, see 2-Ethoxyethanol AI3-01238, see Acetone AI3-01239, see Nitrobenzene AI3-01240, see I idine AI3-01256, see Decahydronaphthalene AI3-01288, see ferf-Butyl alcohol AI3-01445, see Bis(2-chloroethoxy)methane AI3-01501, see 2,4-Toluene diisocyanate AI3-01506, see p,p -DDT AI3-01535, see 2,4-Dinitrophenol AI3-01537, see 2-Chloronaphthalene... 

Hydroxy-4b/ -methyI-7-ethylenedioxy-l,2,3,4,4aa, 4b/ , 5,6,7,8,10,10a/ -dodecahydrophenanthren-l-one.184 To a solution of 2 g (6.9 mmoles) of 4b/ -methyl-7-ethylenedioxy-1,2,3,4,4aa, 4b) ,5,6,7,8,10,1 Oaa-dodecahydro-phenanthrene-1 / ,4/ -diol in 50 ml (0.48 mole) of cyclohexanone and 45 ml of anhydrous benzene is added a solution of 2 g (9.7 mmoles) of freshly distilled aluminum isopropoxide in 5 ml of benzene. The mixture is heated at reflux for 16 hr. After cooling the reaction mixture is treated dropwise with 4 ml of water. The precipitated aluminum salts are collected by filtration and thoroughly washed with benzene. The filtrate is concentrated initially at aspirator pressure, then finally at 0.1 mm at 135-140° to leave a crystalline residue. The residue is triturated with petroleum ether-ether (1 1) and filtered. After washing with the same solvent, the residue is recrystallized from acetone to give 1.35 g of 4/ -hydroxy-4b/ -methyl-7-ethylenedioxy-l,2,3,4,4aa,4b/ ,5, 6,7,8,10,10aa-dodecahydrophenanthren-l-one mp 218-219.5° (68%). 

The first stage in the production of anthracene is the recovery of a 25 to 30% anthracene concentrate by crystallization, which can be carried out in two stages to increase the yield. The crystallizate, known as anthracene cake , is generally concentrated to around 50% by vacuum distillation. The main co-boiling compound of 50 s anthracene is phenanthrene while carbazole is reduced to below 2%. Subsequent refining to yield pure anthracene , containing over 95%, is normally achieved by recrystallization in polar solvents, such as acetophenone, mixtures of cyclohexanol/cyclohexanone or N-methylpyrrolidone in addition, distillation or azeotropic distillation with ethylene glycol can be used for purification. 

Angular polyarenes. A soln. of startg. aldehyde and cyclohexanone trimethylsilyl enolether in methylene chloride under N2 treated dropwise at —78° with excess 1 M TiCl4 in the same solvent, after stirring at that temp, for 2 h the mixture allowed to warm to room temp., stirred for an additional 48 h, then quenched with ice-water -> 1,2,3,4-tetrahydrochrysene (Y 65%), treated with 2 eqs. 2,3-dichloro-5,6-dicyanoqui-none in refluxing benzene for 3 h chrysene (Y 77%). F.e. inch phenanthrene ring and peri-fused chrysenes s. P. Di Raddo, R.G. Harvey, Tetrahedron Letters 29, 3885-6 (1988). 

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