1: KOH / dimethylsulfoxide 2: methanol View Scheme

1: chloroform; aqueous nitric acid 2: chloroform; alkaline aqueous sodium hypochlorite solution View Scheme

1: bromine; diethyl ether 2: benzene View Scheme

bromine in benzene 2 h; Heating / reflux;

[(η5-C5Me5)2Rh2(μ-Cl)2Cl2]; oxygen; caesium carbonate in methanol T=65°C; 48 h; Sealed tube;

1: [{(η5-C5Me5)RhCl}2(μ-Cl)2]; (NH4)2S2O8 / water / 3 h / 110 °C / |Inert atmosphere; |Sealed tube 2: [{(η5-C5Me5)RhCl}2(μ-Cl)2]; (NH4)2S2O8 / water / 12 h / 110 °C / |Inert atmosphere; |Sealed tube View Scheme

potassium hydroxide in ethanol T=95°C; Friedlaender synthesis;

1: 94 percent / 10percent NaOH / ethanol / Ambient temperature 2: 87 percent / acetic acid / 2-ethoxy-ethanol; H2O / 0.08 h / 110 - 120 °C 3: 91 percent / NaOH / H2O; ethanol / 4 h / Heating 4: 94 percent / H2, 1percent aq.PdCl2, Norit / acetic acid / 760 Torr / Ambient temperature 5: 86 percent / POCl3, K2CO3 / acetonitrile / 2.5 h / 55 - 60 °C 6: 1.) TiCl4, 2.) NaBH4 / 1.) CHCl3, a) RT, 2.5 h, b) reflux, 30 min, 2.) MeOH, RT, overnight 7: 91 percent / CHCl3 / 3 h / Heating 8: 89 percent / DDQ / benzene / 2 h / Heating 9: 77 percent / OsO4, pyridine / 2 h / Ambient temperature 10: 70 percent / HIO4*2H2O / H2O; dioxane / 2 h / Ambient temperature 11: 92 percent / K2CO3 / dimethylformamide / 2 h / Ambient temperature 12: 49 percent / 1.) p-toluenesulfonic acid, 2.) aq. 10percent HCl / xylene / 7.5 h / Heating 13: 76 percent / NaBH4 / methanol / 0.5 h / Ambient temperature View Scheme

1: 3',4'-(methylenedioxy)acetophenone With sodium ethanolate in diethyl ether T=20°C; 0.25 h; 2: formic acid ethyl ester in diethyl ether T=20°C; 3 h; 3: ethyl bromide in diethyl ether T=20°C; 24 h; Further stages.;

sulfuryl dichloride in dichloromethane T=0°C; 1.5 h;