Multistep reaction.;

hydrogenchloride in ethanol 6 h; Ambient temperature; Yield given;

samarium diiodide; ytterbium(III) triflate in tetrahydrofuran T=-20°C; Yield given. Yields of byproduct given;

1.1: benzaldehyde / Rh2(OAc)4 / CH2Cl2 / 11 h / 0 °C 1.2: 61 percent / p-TsOH / methanol / 2 h / 20 °C 2.1: HCl; H2 / Pd(OH)2/C / ethanol / 15 h / 20 °C / 760 Torr 2.2: 77 percent / NaHCO3 / ethyl acetate / 0.25 h / 0 °C 3.1: 89 percent / LiOH*H2O / tetrahydrofuran; methanol; H2O / 1 h / 20 °C View Scheme

1.1: benzaldehyde / Rh2(OAc)4 / CH2Cl2 / 11 h / 0 °C 1.2: 61 percent / p-TsOH / methanol / 2 h / 20 °C 2.1: HCl; H2 / Pd(OH)2/C / ethanol / 15 h / 20 °C / 760 Torr 2.2: 77 percent / NaHCO3 / ethyl acetate / 0.25 h / 0 °C View Scheme