magnesium in methanol 5 h; Inert atmosphereReflux;

sodium tetrahydroborate in methanol T=20°C; 2 h; Inert atmosphere;

1: K2CO3 / acetone / 20 h / Heating 2: NaOH / ethanol; H2O / 5 h / Heating 3: SOCl2 / benzene / 8 h / Heating 4: 42 percent / AlCl3 / CH2Cl2 / 1.) 5 h, -65 deg C, 2.) 12 h, room temp. 5: 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 View Scheme

1: 72 percent / p-TsOH, molecular sieves / benzene / 2 h / Heating 2: 92 percent / H2 / PtO2 / acetic acid 3: 92 percent / Na / liquid ammonia / 0.5 h View Scheme