1: 0.56 g / phosphonium iodide, AcOH 2: 0.51 g / pyridine / 15 h / -5 °C 3: 0.30 g / NaI / acetone / 16 h / Heating 4: 0.26 g / NaBH4 / dimethylformamide / 1 h / 80 °C 5: 0.19 g / conc. H2SO4 / 6 h / Heating 6: 0.14 g / LiAlH4 / tetrahydrofuran / 24 h / Ambient temperature View Scheme

potassium meta-periodate

potassium meta-periodate; sulfuric acid in methanol T=40°C; 0.166667 h;

potassium meta-periodate; sulfuric acid in methanol; water T=20 - 40°C; 0.166667 h;

potassium meta-periodate; sulfuric acid in methanol T=40°C; 0.166667 h;

1: pyridine 2: oxalyl chloride/pyridine / benzene 3: 1.) triethylamine; 2.) 25percent HCl / 1.) chloroform, 3 h, 35 deg C; 2.) 5 h, reflux 4: 85 percent / NaOH / methanol / 1 h / Heating 5: 3.5 g / hydrazine hydrate / ethane-1,2-diol / 140 deg C, 1 h then 195 deg C, 6 h 6: pyridine 7: 3.62 g / lead tetraacetate, iodine / CCl4 8: 1.5 g / Zn/HCl / dioxane 9: perchloric acid 10: 1.2 g / CrO3/pyridine / CH2Cl2 / 0.25 h / 20 °C 11: 1.) Mg,I2 / 1 h, reflux 12: 0.675 g / pyridine / 0 °C 13: 1.) sodium iodide, zinc; 2.) dilute acid / 1.) reflux, glyme 14: 1.) HBr; 2.) NaOH / 1.) 15 h, rt., AcOH; 2.) water, reflux, 6 h View Scheme

1: toluene / 18 h / Heating 2: 20 h / Heating 3: 99 percent / H2 / 5percent Pd/C / diethyl ether / 760 Torr View Scheme

1: 89 percent / triethyl orthoformate-benzoic acid / Heating 2: 77 percent / BF3-etherate / methanol / 0.25 h / Heating View Scheme

1: potassium meta-periodate; sulfuric acid / methanol; water / 0.17 h / 40 °C 2: lithium aluminium tetrahydride / diethyl ether / 6 h / |Reflux 3: pyridine / 20 °C 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