sulfuric acid 24 h; Heating;

in methanol 4 h; Heating;

1: 95 percent / methanol / 4 h / Heating 2: 90 percent / lead(IV)-acetate / benzene / 12 h / 25 °C 3: 50 percent / 1. NaHMDS / tetrahydrofuran / 1. 1h reflux 2. -78 deg C, 1h 3. 25 deg C, 20h 4: LiAlH4 / diethyl ether / 3 h / 25 °C 5: 80 percent / PBr3 / 1 h / 85 °C 6: acetonitrile / 24 h / Heating 7: 60 percent / 1. NaHMDS / tetrahydrofuran / 1. -78 deg C, 1h 2. 25 deg C, 20h View Scheme

sodium hydroxide T=375°C;

1: HCl 2: 85 percent / NaIO4 / acetonitrile; CH2Cl2; H2O / 0.5 h View Scheme

(i) aq. HCl, (ii) NaIO4; Multistep reaction;

1: 52.5 g / 5percent methanolic HCl / 48 h / Ambient temperature 2: 38 g / NaIO4 / ethanol; H2O / 1 h / 35 °C 3: 101 g / pyridine / 1.) RT, 24 h, 2.) reflux, 4 h 4: 40 g / 10percent aq. NaOH / 4 h / Heating 5: 55 percent / 60percent H2SO4 / 2.5 h / 130 °C 6: 70 percent / polyphosphoric acid / 2.5 h / 100 °C 7: 22.5 g / 15percent methanolic HCl / 30 h / Ambient temperature View Scheme

1: 52.5 g / 5percent methanolic HCl / 48 h / Ambient temperature 2: 38 g / NaIO4 / ethanol; H2O / 1 h / 35 °C 3: 101 g / pyridine / 1.) RT, 24 h, 2.) reflux, 4 h 4: 40 g / 10percent aq. NaOH / 4 h / Heating 5: 55 percent / 60percent H2SO4 / 2.5 h / 130 °C 6: 70 percent / polyphosphoric acid / 2.5 h / 100 °C 7: 22.5 g / 15percent methanolic HCl / 30 h / Ambient temperature 8: 9.62 g / NaBH4 / methanol / 2 h / Ambient temperature 9: 9.8 g / pyridine 10: 7.8 g / NaOH/85percent aq. MeOH / 2.5 h / Heating 11: 6.2 g / Jones' reagent / acetone / 0.5 h / 0 - 5 °C 12: 0.18 g / diethyl ether View Scheme

1: 52.5 g / 5percent methanolic HCl / 48 h / Ambient temperature 2: 38 g / NaIO4 / ethanol; H2O / 1 h / 35 °C 3: 101 g / pyridine / 1.) RT, 24 h, 2.) reflux, 4 h 4: 40 g / 10percent aq. NaOH / 4 h / Heating View Scheme

1: 98 percent / conc. sulfuric acid / 24 h / Heating 2: 70 percent / lead tetraacetate / benzene 3: n-BuLi / toluene / 2 h / 25 °C View Scheme