1: sodium hydroxide / methanol 2: thionyl chloride / CH2Cl2 / Heating 3: CH2Cl2 / 20 °C 4: bromotrichloromethane / CH2Cl2 / -10 °C / Irradiation View Scheme

1: sodium hydroxide / methanol 2: thionyl chloride / CH2Cl2 / Heating 3: CH2Cl2 / 20 °C 4: CH2Cl2 / 20 °C / Irradiation 5: tetra-n-butylammonium fluoride / tetrahydrofuran / 20 °C View Scheme

1: 80 percent / aq. KOH / ethanol / 1.67 h / 90 °C 2: 77 percent / diethyl ether / 0.5 h 3: 40 percent / NaOMe / methanol / 96 h / Ambient temperature 4: 95 percent / m-chloroperbenzoic acid, disodium hydrogenphosphate / CH2Cl2 / 24 h / Ambient temperature 5: 98 percent / LiAlH4 / diethyl ether / 2 h / Ambient temperature 6: 100 percent / KH / tetrahydrofuran / 0.5 h / Ambient temperature View Scheme