1: 65.7 percent / KOH / ethanol / Ambient temperature 2: 85.7 percent / SOCl2 / toluene / Heating 3: NaN3 / H2O; acetone / 0 °C 4: benzene / Heating 5: 77.8 percent / LiAlH4 / diethyl ether / Ambient temperature 6: 2.) NEt3 / 1.) 3 h, 0 deg C, ether, 2.) 20 h, r.t., ether View Scheme

1: 85.7 percent / SOCl2 / toluene / Heating 2: NaN3 / H2O; acetone / 0 °C 3: benzene / Heating 4: 77.8 percent / LiAlH4 / diethyl ether / Ambient temperature 5: 2.) NEt3 / 1.) 3 h, 0 deg C, ether, 2.) 20 h, r.t., ether View Scheme

1: 77.8 percent / LiAlH4 / diethyl ether / Ambient temperature 2: 2.) NEt3 / 1.) 3 h, 0 deg C, ether, 2.) 20 h, r.t., ether View Scheme

1: NaN3 / H2O; acetone / 0 °C 2: benzene / Heating 3: 77.8 percent / LiAlH4 / diethyl ether / Ambient temperature 4: 2.) NEt3 / 1.) 3 h, 0 deg C, ether, 2.) 20 h, r.t., ether View Scheme

triethylamine 1.) 3 h, 0 deg C, ether, 2.) 20 h, r.t., ether; Yield given. Multistep reaction. Yields of byproduct given;