1: 41 percent / 5N HCl, NaBH3CN, 3 Angstroem molecular sieve / ethanol / 72 h / Ambient temperature 2: tetraline / 10percent Pd/C / 1 h / Heating View Scheme

palladium 10 on activated carbon; zinc T=150°C; 40 h; Autoclave;

1: 95 percent / 0.25 h / 0 °C 2: 91 percent / benzene / 1.) r.t., 2 h, 2.) reflux, 10 h 3: 52 percent / NaBH4, H2O / methanol / 1.) 0 deg C, 15 min, 2.) r.t., 16 h 4: 34 percent / LiAlH4 / tetrahydrofuran / 1.) 0 deg C, 15 min, 2.) r.t., 12 h 5: tetraline / 10percent Pd/C / 1 h / Heating View Scheme

1: 34 percent / LiAlH4 / tetrahydrofuran / 1.) 0 deg C, 15 min, 2.) r.t., 12 h 2: tetraline / 10percent Pd/C / 1 h / Heating View Scheme

1: 91 percent / benzene / 1.) r.t., 2 h, 2.) reflux, 10 h 2: 52 percent / NaBH4, H2O / methanol / 1.) 0 deg C, 15 min, 2.) r.t., 16 h 3: 34 percent / LiAlH4 / tetrahydrofuran / 1.) 0 deg C, 15 min, 2.) r.t., 12 h 4: tetraline / 10percent Pd/C / 1 h / Heating View Scheme

1,2,3,4-tetrahydro-naphthalene; palladium on activated charcoal 1 h; Heating;

nickel