sodium hydroxide in ethanol Heating;

1: PdCl2,CuCl / dimethylformamide; H2O / 24.5 h / Ambient temperature 2: 74 percent / KOH / ethanol / 1 h / Heating 3: 98 percent / p-TsOH / benzene / Heating; overnight 4: 1) ozone, 2) LiAlH4 / 1) CH2Cl2, -60 deg C, 2) dry THF, -20 to -40 deg C 5: p-TsOH / tetrahydrofuran; H2O / 3 h / Heating View Scheme

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