sulfuric acid; nitric acid 1.) H2O, 160-170 deg C, 24 h; Multistep reaction;

hydrogen fluoride 90 h; Ambient temperature;

1: 0.75 h / 200 - 210 °C 2: 94 percent / HF / 90 h / Ambient temperature View Scheme

sodium ethanolate 1.) benzene, 1 h. 2.) benzene, 24 h; Yield given. Multistep reaction;

1: 1.) sodium ethoxide / 1.) benzene, 1 h. 2.) benzene, 24 h 2: 1.) sodium ethoxide / 1.) benzene, 2 h, 2.) DMF, 100 deg C, 20 h View Scheme

1: 1.) sodium ethoxide / 1.) benzene, 1 h. 2.) benzene, 24 h 2: 1.) sodium ethoxide / 1.) benzene, 2 h, 2.) DMF, 100 deg C, 20 h 3: 93 percent / NH3 / methanol / 336 h / Ambient temperature View Scheme

1: 1.) sodium ethoxide / 1.) benzene, 1 h. 2.) benzene, 24 h 2: 1.) sodium ethoxide / 1.) benzene, 2 h, 2.) DMF, 100 deg C, 20 h 3: 48percent HBr, glacial acetic acid / 120 h / Heating 4: H2SO4 View Scheme

1: 1.) sodium ethoxide / 1.) benzene, 1 h. 2.) benzene, 24 h 2: 1.) sodium ethoxide / 1.) benzene, 2 h, 2.) DMF, 100 deg C, 20 h 3: 48percent HBr, glacial acetic acid / 120 h / Heating 4: H2SO4 5: 27.6 percent / NH3 / methanol / 168 h / Ambient temperature View Scheme

1: 1.) sodium ethoxide / 1.) benzene, 1 h. 2.) benzene, 24 h 2: 1.) sodium ethoxide / 1.) benzene, 2 h, 2.) DMF, 100 deg C, 20 h 3: 48percent HBr, glacial acetic acid / 120 h / Heating 4: H2SO4 5: 27.6 percent / NH3 / methanol / 168 h / Ambient temperature 6: 51 percent / NaBH4 / ethanol / 20 h / Ambient temperature View Scheme