boron tribromide in dichloromethane 2 h; Ambient temperature;

1.1: n-butyllithium / hexane; tetrahydrofuran / 2 h / 0 - 20 °C / |Inert atmosphere 1.2: 0.5 h / -80 °C / |Inert atmosphere 2.1: N-bromosuccinmide / tetrachloromethane / 3 h / |Reflux 3.1: lithium diisopropyl amide; n-butyllithium / hexane; tetrahydrofuran / -80 °C / |Inert atmosphere 3.2: -80 - 20 °C / |Inert atmosphere 4.1: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 0 - 20 °C 5.1: ammonium cerium (IV) nitrate / acetonitrile; water / 0.5 h / 0 °C View Scheme

potassium hydroxide in water; dimethyl sulfoxide T=20°C; 1.5 h;

1: 2-methoxy-1,4-naphthalenequinone With sodium dithionite in 1,4-dioxane; water 1 h; 2: dimethyl sulfate With potassium hydroxide T=20°C; 3 h;

sodium hydroxide Heating; Yield given;

potassium hydroxide; acetic acid 1.) electrolysis, 20 deg C, 0.8 h, 2.) acetone, 20 min; Yield given. Multistep reaction. Yields of byproduct given;

sodium tetrahydroborate; palladium dichloride in methanol 1 h; Ambient temperature;

1: 1.8 g / O2, K / 2-methyl-propan-2-ol / 4 h / Ambient temperature 2: 1.0 g / conc. HCl / 3 h / Heating 3: 1.) SnCl2, conc. HCl; 2.) 50percent KOH / 1.) EtOH, r.t., 1 h; 2.) reflux, 1 h 4: 2 mg / NaBH4, PdCl2 / methanol / 1 h / Ambient temperature View Scheme

1: SOCl2 / 1 h / Heating 2: AlCl3 / CS2 / 3 h / Heating 3: 1.8 g / O2, K / 2-methyl-propan-2-ol / 4 h / Ambient temperature 4: 1.0 g / conc. HCl / 3 h / Heating 5: 1.) SnCl2, conc. HCl; 2.) 50percent KOH / 1.) EtOH, r.t., 1 h; 2.) reflux, 1 h 6: 2 mg / NaBH4, PdCl2 / methanol / 1 h / Ambient temperature View Scheme

1: 1.0 g / conc. HCl / 3 h / Heating 2: 1.) SnCl2, conc. HCl; 2.) 50percent KOH / 1.) EtOH, r.t., 1 h; 2.) reflux, 1 h 3: 2 mg / NaBH4, PdCl2 / methanol / 1 h / Ambient temperature View Scheme