sodium hydroxide in methanol 2.5 h; Heating;

sodium tetrahydroborate; nickel dichloride in tetrahydrofuran; methanol 1 h; Ambient temperature;

1: 94 percent / 10percent NaOH / methanol / 2.5 h / Heating 2: 90 percent / LiAlH4 / diethyl ether / 3 h / Heating 3: 77 percent / SOCl2 / benzene / 1 h / Heating 4: 75 percent / H2O; dimethylsulfoxide / 2 h / 40 - 50 °C View Scheme

1: 94 percent / 10percent NaOH / methanol / 2.5 h / Heating 2: 90 percent / LiAlH4 / diethyl ether / 3 h / Heating 3: 77 percent / SOCl2 / benzene / 1 h / Heating 4: 75 percent / H2O; dimethylsulfoxide / 2 h / 40 - 50 °C 5: diisobutylaluminium hydride / benzene / 3 h / Ambient temperature View Scheme