1: AlCl3 / nitrobenzene / 0 - 20 °C 2: NaOCl, NaOH / H2O / Heating 3: 92 percent / conc. H2SO4 / 96 h / Heating 4: 95 percent / LiBH4 / tetrahydrofuran 5: BaMnO4 / CH2Cl2 / 15 h / Heating 6: 1.) p-toluenesulfonic acid hydrate, 2.) NaBH4 / 1.) PhCH3, reflux, 2 h, 2.) EtOH, RT, overnight View Scheme

1: NaOCl, NaOH / H2O / Heating 2: 92 percent / conc. H2SO4 / 96 h / Heating 3: 95 percent / LiBH4 / tetrahydrofuran 4: BaMnO4 / CH2Cl2 / 15 h / Heating 5: 1.) p-toluenesulfonic acid hydrate, 2.) NaBH4 / 1.) PhCH3, reflux, 2 h, 2.) EtOH, RT, overnight View Scheme

1: 92 percent / conc. H2SO4 / 96 h / Heating 2: 95 percent / LiBH4 / tetrahydrofuran 3: BaMnO4 / CH2Cl2 / 15 h / Heating 4: 1.) p-toluenesulfonic acid hydrate, 2.) NaBH4 / 1.) PhCH3, reflux, 2 h, 2.) EtOH, RT, overnight View Scheme

1: BaMnO4 / CH2Cl2 / 15 h / Heating 2: 1.) p-toluenesulfonic acid hydrate, 2.) NaBH4 / 1.) PhCH3, reflux, 2 h, 2.) EtOH, RT, overnight View Scheme

1: 95 percent / LiBH4 / tetrahydrofuran 2: BaMnO4 / CH2Cl2 / 15 h / Heating 3: 1.) p-toluenesulfonic acid hydrate, 2.) NaBH4 / 1.) PhCH3, reflux, 2 h, 2.) EtOH, RT, overnight View Scheme

sodium tetrahydroborate; toluene-4-sulfonic acid 1.) PhCH3, reflux, 2 h, 2.) EtOH, RT, overnight; Yield given. Multistep reaction;