1: SOCl2 / benzene / 8 h / Heating 2: 42 percent / AlCl3 / CH2Cl2 / 1.) 5 h, -65 deg C, 2.) 12 h, room temp. 3: 68 percent / NaBH4 / methanol / 1.) 1 h, room temp., 2.) 0.5 h, reflux View Scheme

1: SOCl2 / benzene / 8 h / Heating 2: 42 percent / AlCl3 / CH2Cl2 / 1.) 5 h, -65 deg C, 2.) 12 h, room temp. 3: 68 percent / NaBH4 / methanol / 1.) 1 h, room temp., 2.) 0.5 h, reflux 4: 72 percent / p-TsOH, molecular sieves / benzene / 2 h / Heating 5: 92 percent / H2 / PtO2 / acetic acid 6: 92 percent / Na / liquid ammonia / 0.5 h View Scheme