lithium aluminium tetrahydride in diethyl ether 1.) 0 deg C, 2.) ambient temp., 4h;

1: 94 percent / benzene / 4 h / 40 - 50 °C 2: 85 percent / LiAlH4 / diethyl ether / 1.) 0 deg C, 2.) ambient temp., 4h View Scheme

1: 1.) sodium iodide, chlorotrimethylsilane, 2.) Zn-Cu couple / 1.) ether, 25 deg C, 1h, 2.) ether, 2h 2: 94 percent / benzene / 4 h / 40 - 50 °C 3: 85 percent / LiAlH4 / diethyl ether / 1.) 0 deg C, 2.) ambient temp., 4h View Scheme

1: 92 percent / LiAlH4 / diethyl ether / 0 °C 2: 1.) sodium iodide, chlorotrimethylsilane, 2.) Zn-Cu couple / 1.) ether, 25 deg C, 1h, 2.) ether, 2h 3: 94 percent / benzene / 4 h / 40 - 50 °C 4: 85 percent / LiAlH4 / diethyl ether / 1.) 0 deg C, 2.) ambient temp., 4h View Scheme