1: 95 percent / H2 / Pd/C / methanol / 1 h / 20 °C / 760 Torr 2: 82 percent / conc. H2SO4 / 16 h / Heating 3: 82 percent / LiAlH4 / tetrahydrofuran / 2 h / Heating 4: 1.) aq. NaNO2, aq. HCl / 1.) -5 deg C, 30 min, 2.) H2O, 0 deg C, 2 h View Scheme

1: LiAlH4 / tetrahydrofuran View Scheme

1: 82 percent / conc. H2SO4 / 16 h / Heating 2: 82 percent / LiAlH4 / tetrahydrofuran / 2 h / Heating 3: 1.) aq. NaNO2, aq. HCl / 1.) -5 deg C, 30 min, 2.) H2O, 0 deg C, 2 h View Scheme

1: 82 percent / LiAlH4 / tetrahydrofuran / 2 h / Heating 2: 1.) aq. NaNO2, aq. HCl / 1.) -5 deg C, 30 min, 2.) H2O, 0 deg C, 2 h View Scheme

Multistep reaction;

hydrogenchloride; sodium nitrite 1.) -5 deg C, 30 min, 2.) H2O, 0 deg C, 2 h; Yield givenMultistep reaction;