1: 94 percent / p-toluenesulfonic acid / toluene / Heating 2: 1) Hg(OAc)2 / 1) 85 deg C, aq. AcOH, 5 h, 2) 0 deg C, 1 h View Scheme

lithium aluminium tetrahydride 1) 0 deg C, THF, 1 h, 2) water; Yield given. Multistep reaction;

1: 20 percent / LiAl(OEt)3H / diethyl ether / 0.25 h / 0 °C 2: 55 percent / NaCNBH3 / methanol / 0.5 h / Ambient temperature; pH = 6 3: CH2Cl2 / 1.) 0 deg C., 15 min, 2.) r. t., 10 min. 4: Bu4NBr / 1,2-dichloro-benzene / 0.25 h / Heating 5: LiAlH4 / diethyl ether / 1 h 6: 65 percent / 6 M HCl / 2 h / Heating View Scheme

1: LiAlH4 / tetrahydrofuran / 0.33 h 2: 96 percent / CH2Cl2 / 0.25 h 3: Bu4NBr / 1,2-dichloro-benzene / 1 h / Heating 4: LiAlH4 / tetrahydrofuran / 3 h 5: Et3N / CH2Cl2 / 1.) ice cooled, 1 h, 2.) r.t., 1 h 6: 92 percent / 6 M HCl / 3 h / Heating View Scheme