1: 1N NaOH / 1 h / 0 °C 2: thionyl chloride / benzene 3: diethyl ether / 3 h / 0 °C 4: aq. NaHCO3 / methanol View Scheme

1: diethyl ether / 3 h / 0 °C 2: aq. NaHCO3 / methanol View Scheme

1: 22 percent / copper(II) chloride / CHCl3 / 25 h / Heating 2: 83 percent / NaBH4 / methanol / 0.5 h / 0 °C 3: 90 percent / hydrogen / 10percent palladium-carbon / ethyl acetate 4: 99 percent / diethyl ether / 2 h / 0 °C 5: 59 percent / p-TsOH / benzene / 96 h / Ambient temperature View Scheme

1: 22 percent / copper(II) chloride / CHCl3 / 25 h / Heating 2: 83 percent / NaBH4 / methanol / 0.5 h / 0 °C 3: 89 percent / Li/liq. NH3 / tetrahydrofuran / 0.02 h / -78 °C 4: pyridine / 3 h / 0 °C 5: 73 percent / dimethylsulfoxide / 7 h / 60 - 70 °C View Scheme

1: 22 percent / copper(II) chloride / CHCl3 / 25 h / Heating 2: 83 percent / NaBH4 / methanol / 0.5 h / 0 °C 3: 90 percent / hydrogen / 10percent palladium-carbon / ethyl acetate 4: pyridine / 3 h / 0 °C 5: 80 percent / dimethylsulfoxide / 7 h / 60 - 70 °C View Scheme