sodium; benzene

1: 1.) aq. HCl, NaNO2 / 1.) 0 deg C, 2.) 0-2 deg C 2: 1.) NaH / 1.) DMF, from RT to 70 deg C, 2.) DMF, 70 deg C, 2 h 3: 2.3 g / H2 / 10percent Pd/C / ethanol / 760 Torr View Scheme

1: 86 percent / dimethylformamide / 20 - 80 °C 2: 0.58 h / 264 - 282 °C 3: NaOH / methanol / 12 h / Heating 4: LiH / dimethylformamide / -60 °C 5: SbF3 / 2 h / 150 - 160 °C View Scheme

1: 86 percent / dimethylformamide / 20 - 80 °C 2: 0.58 h / 264 - 282 °C 3: NaOH / methanol / 12 h / Heating 4: LiH / dimethylformamide / -60 °C 5: SbF3 / 2 h / 150 - 160 °C 6: 98 percent / H2O2; H2O / acetic acid / 3 h / 80 - 88 °C 7: 84 percent / H2SO4*SO3 / CH2Cl2 / 20 h / 0 - 42 °C View Scheme

1: 86 percent / dimethylformamide / 20 - 80 °C 2: 0.58 h / 264 - 282 °C 3: NaOH / methanol / 12 h / Heating 4: LiH / dimethylformamide / -60 °C 5: SbF3 / 2 h / 150 - 160 °C 6: 98 percent / H2O2; H2O / acetic acid / 3 h / 80 - 88 °C 7: 79 percent / H2SO4*SO3 / CH2Cl2 / 1.5 h / 20 °C 8: 92 percent / acetonitrile / 1.5 h / 60 °C View Scheme

1: 86 percent / dimethylformamide / 20 - 80 °C 2: 0.58 h / 264 - 282 °C 3: NaOH / methanol / 12 h / Heating 4: LiH / dimethylformamide / -60 °C 5: SbF3 / 2 h / 150 - 160 °C 6: 98 percent / H2O2; H2O / acetic acid / 3 h / 80 - 88 °C View Scheme

1: 86 percent / dimethylformamide / 20 - 80 °C 2: 0.58 h / 264 - 282 °C 3: NaOH / methanol / 12 h / Heating View Scheme

T=190°C; P=15200 Torr; 24 h;

1: 40 percent / 24 h / 190 °C / 15200 Torr 2: 100 percent / K2CO3 / 12 h / 50 °C 3: LiAlH4 / tetrahydrofuran / Heating 4: MnO2 / diethyl ether / 12 h / 20 °C 5: tBuOK / diethyl ether / 0.17 h / 0 °C View Scheme