copper(l) chloride; palladium dichloride in water; N,N-dimethyl-formamide 24.5 h; Ambient temperature; Yield given;

1: 1) NaH (50percent in mineral oil) / 1) dry benzene, 0 deg C, 2) dry benzene, 5 h 30 min, reflux 2: PdCl2,CuCl / dimethylformamide; H2O / 24.5 h / Ambient temperature View Scheme

1: 1) NaH (50percent in mineral oil) / 1) benzene, 2) reflux, 6 h 2: 1) NaH (50percent in mineral oil) / 1) dry benzene, 0 deg C, 2) dry benzene, 5 h 30 min, reflux 3: PdCl2,CuCl / dimethylformamide; H2O / 24.5 h / Ambient temperature View Scheme

1: 74 percent / KOH / ethanol / 1 h / Heating 2: 98 percent / p-TsOH / benzene / Heating; overnight 3: 1) ozone, 2) LiAlH4 / 1) CH2Cl2, -60 deg C, 2) dry THF, -20 to -40 deg C 4: p-TsOH / tetrahydrofuran; H2O / 3 h / Heating View Scheme