lithium aluminium tetrahydride in tetrahydrofuran T=0°C; 1 h;

hydrogenchloride in ethanol 3 h; Heating;

1: 98.6 percent / benzene / 2 h / Heating 2: 94.4 percent / H2 / platinum oxide / ethanol / 2 h / Ambient temperature 3: 31.1 percent / potassium carbonate / 0.5 h / 40 °C 4: 1.) conc. HCl, 2.) aq. NH4OH, sodium borohydride / 1) ethanol, reflux, 2 h; 2) ethanol, room temperature, 2 h View Scheme

lithium aluminium tetrahydride in tetrahydrofuran 3 h; Heating;

1: 98.6 percent / benzene / 2 h / Heating 2: 94.4 percent / H2 / platinum oxide / ethanol / 2 h / Ambient temperature 3: 31.1 percent / potassium carbonate / 0.5 h / 40 °C 4: 1.) conc. HCl, 2.) aq. NH4OH, sodium borohydride / 1) ethanol, reflux, 2 h; 2) ethanol, room temperature, 2 h View Scheme

1: 3.76 g / Heating 2: 2.26 g / n-Bu3N / Pd(OAc)2, PPh3 / 30 h / 100 °C 3: 1.02 g / HCl / ethanol / 2 h / Heating 4: 600 mg / lithium aluminium hydride / tetrahydrofuran / 60 h / Heating View Scheme

1: 2.26 g / n-Bu3N / Pd(OAc)2, PPh3 / 30 h / 100 °C 2: 1.02 g / HCl / ethanol / 2 h / Heating 3: 600 mg / lithium aluminium hydride / tetrahydrofuran / 60 h / Heating View Scheme

hydrogenchloride 1.) 115-125 deg C, 1 h; 2.) EtOH, heating, 2 h; Yield given. Multistep reaction;

1: 59 percent / 1) lithium diisopropylamide 2) acetic anhydride, sodium acetate / tetrahydrofuran / 1) a) 1h -78 deg C b) 3.75h -78 -> 25 deg C 2) 1h reflux 2: 91 percent / toluene / 24 h / 120 °C 3: 97 percent / 1.0N aqueous NaOH / methanol; tetrahydrofuran / 10 h / 25 °C 4: 1) 1N aqueous KOH 2) oxalyl chloride / 1) MeOH, 25 deg C 2) dry benzene, ca.3h, 25 deg C 5: 76 percent / tetrahydrofuran / 1 h / -78 °C 6: 62 percent / m-CPBA / CH2Cl2 / 25 °C 7: 70 percent / lithium aluminum hydride / tetrahydrofuran / 1 h / 0 °C View Scheme

1: 74 percent / 10percent aqueous H2SO4 / tetrahydrofuran / 20 h / 25 °C 2: 59 percent / 1) lithium diisopropylamide 2) acetic anhydride, sodium acetate / tetrahydrofuran / 1) a) 1h -78 deg C b) 3.75h -78 -> 25 deg C 2) 1h reflux 3: 91 percent / toluene / 24 h / 120 °C 4: 97 percent / 1.0N aqueous NaOH / methanol; tetrahydrofuran / 10 h / 25 °C 5: 1) 1N aqueous KOH 2) oxalyl chloride / 1) MeOH, 25 deg C 2) dry benzene, ca.3h, 25 deg C 6: 76 percent / tetrahydrofuran / 1 h / -78 °C 7: 62 percent / m-CPBA / CH2Cl2 / 25 °C 8: 70 percent / lithium aluminum hydride / tetrahydrofuran / 1 h / 0 °C View Scheme