potassium carbonate in acetonitrile 16 h; Reflux;

potassium carbonate in N,N-dimethyl-formamide 1.5 h; Heating;

1: 95 percent / conc. H2SO4 / 18 h / Heating 2: NaH / dimethylsulfoxide View Scheme

sulfuric acid 24 h; Heating;

sodium hydride in dimethyl sulfoxide

potassium hydroxide in water 1 h; Heating;

1: 99 percent / LiAlH4 / tetrahydrofuran / 0.5 h / Ambient temperature 2: 96 percent / MnO2 / CH2Cl2 / 6 h / Ambient temperature 3: 79 percent / triethylamine, NaBH3CN / ethanol / 14 h / Ambient temperature 4: 99 percent / ethyl formate / 20 h / Ambient temperature 5: 94 percent / methanesulfonic acid / 1 h / 70 °C / other reagent: polyphosphoric acid 6: 75 percent / p-toluenesulfonic acid monohydrate, chloranil / benzene / 15 h / Ambient temperature; other reagent: benzoquinone 7: 65 percent / lithium diisopropylamide / tetrahydrofuran; hexane / 1.) -50 deg C, 2 h, 2.) room temperature, 3 h 8: 74 percent / m-chloroperbenzoic acid / CH2Cl2 / 24 h / Ambient temperature View Scheme

1: 99 percent / LiAlH4 / tetrahydrofuran / 0.5 h / Ambient temperature 2: 96 percent / MnO2 / CH2Cl2 / 6 h / Ambient temperature 3: 79 percent / triethylamine, NaBH3CN / ethanol / 14 h / Ambient temperature 4: 99 percent / ethyl formate / 20 h / Ambient temperature 5: 94 percent / methanesulfonic acid / 1 h / 70 °C / other reagent: polyphosphoric acid 6: 75 percent / p-toluenesulfonic acid monohydrate, chloranil / benzene / 15 h / Ambient temperature; other reagent: benzoquinone 7: 98 percent / m-chloroperbenzoic acid / CH2Cl2 / 4 h / Ambient temperature 8: 62 percent / triethylamine / acetonitrile / 3 h / Heating 9: 2.) HCl / 1.) THF, hexane, -50 deg C, 25 min, 2.) methanol, reflux, 5 min 10: 85 percent / AlCl3 / benzene / 2 h / Ambient temperature View Scheme

manganese(IV) oxide; lithium aluminium tetrahydride 1.) THF, RT, 2.) CH2Cl2, RT; Yield given. Multistep reaction;

1: 99 percent / LiAlH4 / tetrahydrofuran / 0.5 h / Ambient temperature 2: 96 percent / MnO2 / CH2Cl2 / 6 h / Ambient temperature 3: 79 percent / triethylamine, NaBH3CN / ethanol / 14 h / Ambient temperature 4: 99 percent / ethyl formate / 20 h / Ambient temperature 5: 94 percent / methanesulfonic acid / 1 h / 70 °C / other reagent: polyphosphoric acid 6: 75 percent / p-toluenesulfonic acid monohydrate, chloranil / benzene / 15 h / Ambient temperature; other reagent: benzoquinone 7: 65 percent / lithium diisopropylamide / tetrahydrofuran; hexane / 1.) -50 deg C, 2 h, 2.) room temperature, 3 h 8: 74 percent / m-chloroperbenzoic acid / CH2Cl2 / 24 h / Ambient temperature 9: 61 percent / triethylamine / acetonitrile / 5 h / 70 °C 10: 97 percent / KOH / acetonitrile; H2O / 14 h / Ambient temperature 11: 90 percent / HCl / CH2Cl2 / 1.) room temperature, 24 h, 2.) reflux, 10 h View Scheme