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