in methanol; diethyl ether T=0 - 20°C; 1 h;

sodium iodide; zinc 2.5 h; Heating;

1: Jone's reagent / acetone / 0 - 4 °C 2: sulfuric acid / 20 °C 3: hydrogen; ethylenediamine / ethanol; water View Scheme

1.1: n-butyllithium / tetrahydrofuran; N,N,N',N',N'',N''-hexamethylphosphoric triamide; hexane / 0.5 h / -60 °C 1.2: -20 - 20 °C 2.1: Jone's reagent / acetone / 0 - 4 °C 3.1: sulfuric acid / 20 °C 4.1: hydrogen; ethylenediamine / ethanol; water View Scheme

1.1: toluene-4-sulfonic acid / dichloromethane / 20 °C 2.1: n-butyllithium / tetrahydrofuran; N,N,N',N',N'',N''-hexamethylphosphoric triamide; hexane / 0.5 h / -60 °C 2.2: -20 - 20 °C 3.1: Jone's reagent / acetone / 0 - 4 °C 4.1: sulfuric acid / 20 °C 5.1: hydrogen; ethylenediamine / ethanol; water View Scheme

1: pyridine / 8 h / Heating 2: 69 percent / cupric acetate, lead tetraacetate / pyridine / 4 h / Heating 3: 1.) KMnO4, adogen 464, 2.) aq. NaOH / 1) water, benzene, 12 h, room temperature; 2) reflux, 3 h 4: 92 percent / triethyl orthoformate, benzoic acid / Heating 5: conc. H2SO4 / Heating 6: 92 percent / pyridine / 20 h / -5 °C 7: 80 percent / zinc (dust), NaI / 2.5 h / Heating View Scheme

1: 69 percent / cupric acetate, lead tetraacetate / pyridine / 4 h / Heating 2: 1.) KMnO4, adogen 464, 2.) aq. NaOH / 1) water, benzene, 12 h, room temperature; 2) reflux, 3 h 3: 92 percent / triethyl orthoformate, benzoic acid / Heating 4: conc. H2SO4 / Heating 5: 92 percent / pyridine / 20 h / -5 °C 6: 80 percent / zinc (dust), NaI / 2.5 h / Heating View Scheme

1: sulfuric acid / 20 °C 2: hydrogen; ethylenediamine / ethanol; water View Scheme

1: methanol; toluene-4-sulfonic acid / 2 h / 20 °C 2: Jone's reagent / acetone / 0.33 h / 0 - 20 °C 3: methanol; diethyl ether / 1 h / 0 - 20 °C View Scheme

1: 1.) KMnO4, adogen 464, 2.) aq. NaOH / 1) water, benzene, 12 h, room temperature; 2) reflux, 3 h 2: 92 percent / triethyl orthoformate, benzoic acid / Heating 3: conc. H2SO4 / Heating 4: 92 percent / pyridine / 20 h / -5 °C 5: 80 percent / zinc (dust), NaI / 2.5 h / Heating View Scheme