thionyl chloride

benzene

methanol; sodium Electrolysis.und Behandeln des Reaktionsprodukts mit heisser wss.Natronlauge;

1: 70 percent / Na/ethanol / liquid ammonia / 1 h 2: 92 percent / 1) Na, 2) HMPT / tetrahydrofuran / 1) 12 h, reflux, 2) 3 h, reflux 3: 98 percent / diethyl ether; methanol 4: 71 percent / O3 / CH2Cl2 / -78 °C 5: 85 percent / LiAlH4 / diethyl ether / 12 h / Heating 6: 76 percent / PBr3 / petroleum ether; pyridine / Ambient temperature View Scheme

1: 70 percent / Na/ethanol / liquid ammonia / 1 h 2: 92 percent / 1) Na, 2) HMPT / tetrahydrofuran / 1) 12 h, reflux, 2) 3 h, reflux 3: 98 percent / diethyl ether; methanol 4: 71 percent / O3 / CH2Cl2 / -78 °C 5: 85 percent / LiAlH4 / diethyl ether / 12 h / Heating View Scheme