hydrogenchloride in methanol T=70°C; 0.25 h;

1: 93 percent / KOH / ethanol 2: 87 percent / conc. HCl / methanol; dioxane 3: 92 percent / 30percent H2O2, 5percent NaOH / methanol; dioxane 4: 1.) BF3*Et2O, 2.) NaBH4 / 1.) benzene, 0 deg C, 2.) THF 5: 66 percent / H2 / 10percent Pd-C / methanol 6: BF3-Et2O / 5 °C 7: 66 percent / (i-Pr)2NEt / CH2Cl2 8: 91 percent / 1M NaOH / methanol 9: 95 percent / MnO2 / CH2Cl2 10: 94 percent / NaOH / ethanol 11: 96 percent / 30percent H2O2, 5percent NaOH / methanol 12: 19 percent / conc. HCl / methanol / 70 °C View Scheme

1: 92 percent / 30percent H2O2, 5percent NaOH / methanol; dioxane 2: 1.) BF3*Et2O, 2.) NaBH4 / 1.) benzene, 0 deg C, 2.) THF 3: 66 percent / H2 / 10percent Pd-C / methanol 4: BF3-Et2O / 5 °C 5: 66 percent / (i-Pr)2NEt / CH2Cl2 6: 91 percent / 1M NaOH / methanol 7: 95 percent / MnO2 / CH2Cl2 8: 94 percent / NaOH / ethanol 9: 96 percent / 30percent H2O2, 5percent NaOH / methanol 10: 19 percent / conc. HCl / methanol / 70 °C View Scheme

1: 66 percent / H2 / 10percent Pd-C / methanol 2: BF3-Et2O / 5 °C 3: 66 percent / (i-Pr)2NEt / CH2Cl2 4: 91 percent / 1M NaOH / methanol 5: 95 percent / MnO2 / CH2Cl2 6: 94 percent / NaOH / ethanol 7: 96 percent / 30percent H2O2, 5percent NaOH / methanol 8: 19 percent / conc. HCl / methanol / 70 °C View Scheme

1: 1.) BF3*Et2O, 2.) NaBH4 / 1.) benzene, 0 deg C, 2.) THF 2: 66 percent / H2 / 10percent Pd-C / methanol 3: BF3-Et2O / 5 °C 4: 66 percent / (i-Pr)2NEt / CH2Cl2 5: 91 percent / 1M NaOH / methanol 6: 95 percent / MnO2 / CH2Cl2 7: 94 percent / NaOH / ethanol 8: 96 percent / 30percent H2O2, 5percent NaOH / methanol 9: 19 percent / conc. HCl / methanol / 70 °C View Scheme

1: 87 percent / conc. HCl / methanol; dioxane 2: 92 percent / 30percent H2O2, 5percent NaOH / methanol; dioxane 3: 1.) BF3*Et2O, 2.) NaBH4 / 1.) benzene, 0 deg C, 2.) THF 4: 66 percent / H2 / 10percent Pd-C / methanol 5: BF3-Et2O / 5 °C 6: 66 percent / (i-Pr)2NEt / CH2Cl2 7: 91 percent / 1M NaOH / methanol 8: 95 percent / MnO2 / CH2Cl2 9: 94 percent / NaOH / ethanol 10: 96 percent / 30percent H2O2, 5percent NaOH / methanol 11: 19 percent / conc. HCl / methanol / 70 °C View Scheme

1: 86 percent / potassium carbonate / dimethylformamide / 3 h / Heating 2: 91 percent / ammonium chloride / methanol / 4 h / Heating 3: 94 percent / 1.) n-butyl lithium / hexane; diethyl ether / 1.) -78 deg C, 10 min, 2.) -78 deg C to room temperature, 3 h 4: 93 percent / potassium hydroxide / ethanol / 4 h 5: 87 percent / conc. HCl / dioxane; methanol / 1.5 h / Ambient temperature 6: 92 percent / 30percent H2O2, 5percent NaOH / dioxane; methanol / 3 h / Ambient temperature 7: 1.) boron trifluoride etherate, 2.) sodium borohydride / 1.) benzene, 20 min, 2.) THF, room temperature, 2 h 8: 66 percent / hydrogen / 10percent Pd/C / methanol 9: 77 percent / boron trifluoride etherate / acetic acid / 0.25 h / 5 °C 10: 66 percent / diisopropylethylamine / CH2Cl2 / 3 h / Ambient temperature 11: 91 percent / 1N NaOH / methanol / 1 h / Ambient temperature 12: 95 percent / manganese dioxide / CH2Cl2 / 0.5 h 13: 94 percent / sodium hydroxide / ethanol / 4 h 14: 96 percent / 30percent H2O2, 5percent NaOH / methanol / 4 h / Ambient temperature 15: 19 percent / conc. HCl / methanol / 0.25 h / 70 °C View Scheme

1: 91 percent / ammonium chloride / methanol / 4 h / Heating 2: 94 percent / 1.) n-butyl lithium / hexane; diethyl ether / 1.) -78 deg C, 10 min, 2.) -78 deg C to room temperature, 3 h 3: 93 percent / potassium hydroxide / ethanol / 4 h 4: 87 percent / conc. HCl / dioxane; methanol / 1.5 h / Ambient temperature 5: 92 percent / 30percent H2O2, 5percent NaOH / dioxane; methanol / 3 h / Ambient temperature 6: 1.) boron trifluoride etherate, 2.) sodium borohydride / 1.) benzene, 20 min, 2.) THF, room temperature, 2 h 7: 66 percent / hydrogen / 10percent Pd/C / methanol 8: 77 percent / boron trifluoride etherate / acetic acid / 0.25 h / 5 °C 9: 66 percent / diisopropylethylamine / CH2Cl2 / 3 h / Ambient temperature 10: 91 percent / 1N NaOH / methanol / 1 h / Ambient temperature 11: 95 percent / manganese dioxide / CH2Cl2 / 0.5 h 12: 94 percent / sodium hydroxide / ethanol / 4 h 13: 96 percent / 30percent H2O2, 5percent NaOH / methanol / 4 h / Ambient temperature 14: 19 percent / conc. HCl / methanol / 0.25 h / 70 °C View Scheme

1: 94 percent / 1.) n-butyl lithium / hexane; diethyl ether / 1.) -78 deg C, 10 min, 2.) -78 deg C to room temperature, 3 h 2: 93 percent / potassium hydroxide / ethanol / 4 h 3: 87 percent / conc. HCl / dioxane; methanol / 1.5 h / Ambient temperature 4: 92 percent / 30percent H2O2, 5percent NaOH / dioxane; methanol / 3 h / Ambient temperature 5: 1.) boron trifluoride etherate, 2.) sodium borohydride / 1.) benzene, 20 min, 2.) THF, room temperature, 2 h 6: 66 percent / hydrogen / 10percent Pd/C / methanol 7: 77 percent / boron trifluoride etherate / acetic acid / 0.25 h / 5 °C 8: 66 percent / diisopropylethylamine / CH2Cl2 / 3 h / Ambient temperature 9: 91 percent / 1N NaOH / methanol / 1 h / Ambient temperature 10: 95 percent / manganese dioxide / CH2Cl2 / 0.5 h 11: 94 percent / sodium hydroxide / ethanol / 4 h 12: 96 percent / 30percent H2O2, 5percent NaOH / methanol / 4 h / Ambient temperature 13: 19 percent / conc. HCl / methanol / 0.25 h / 70 °C View Scheme

1: 93 percent / potassium hydroxide / ethanol / 4 h 2: 87 percent / conc. HCl / dioxane; methanol / 1.5 h / Ambient temperature 3: 92 percent / 30percent H2O2, 5percent NaOH / dioxane; methanol / 3 h / Ambient temperature 4: 1.) boron trifluoride etherate, 2.) sodium borohydride / 1.) benzene, 20 min, 2.) THF, room temperature, 2 h 5: 66 percent / hydrogen / 10percent Pd/C / methanol 6: 77 percent / boron trifluoride etherate / acetic acid / 0.25 h / 5 °C 7: 66 percent / diisopropylethylamine / CH2Cl2 / 3 h / Ambient temperature 8: 91 percent / 1N NaOH / methanol / 1 h / Ambient temperature 9: 95 percent / manganese dioxide / CH2Cl2 / 0.5 h 10: 94 percent / sodium hydroxide / ethanol / 4 h 11: 96 percent / 30percent H2O2, 5percent NaOH / methanol / 4 h / Ambient temperature 12: 19 percent / conc. HCl / methanol / 0.25 h / 70 °C View Scheme