sodium hydroxide; bromine in 1,4-dioxane; water T=60°C; Oxidation; 4 h;

1: pyrene With hydrogen; 10 palladium on active carbon in ethyl acetate Hydrogenation; P=2068.59 - 2327.17 Torr; 72 h; 2: acetyl chloride With aluminium trichloride in dichloromethane T=0 - 20°C; Acetylation; 2.5 h;

aluminium trichloride; d-N,a-dimethylphenethylamine in dichloromethane 1.) 0 deg C then RT 2 h;

1: H2 / 10percent Pd on charcoal / ethyl acetate / 72 h / 2844.3 Torr 2: 98 percent / 1.) AlCl3, 2.) ice / CH2Cl2 / 1.) 0 deg C then RT 2 h View Scheme

1: 98 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / benzene / 72 h / Heating 2: 98 percent / NaBH4 / methanol / 2 h 3: 79 percent / p-toluenesulfonic acid / benzene / 20 h / Heating 4: 73 percent / m-chloroperbenzoic acid / CH2Cl2 / 360 h / 4 °C / phosphate buffer (pH 8) View Scheme

1: 98 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / benzene / 72 h / Heating 2: 98 percent / NaBH4 / methanol / 2 h View Scheme