hydrogen; palladium in ethanol

1: 97 percent / H2 / Pd/C / ethanol / 18 h / 2585.74 Torr 2: 90 percent / pyridinium chlorochromate; sodium acetate / CH2Cl2 / 3 h / 20 °C View Scheme

1: hydrogen; 5 palladium on charcoal / dichloromethane / 3.5 h / 3345.86 Torr / |Inert atmosphere; |Autoclave; |Large scale 2: 2,2,6,6-tetramethyl-1-piperidinyloxy, free radical; potassium bromide; sodium hypochlorite; sodium hydrogencarbonate / dichloromethane; water / -10 - 20 °C / pH 9.5 / |Large scale 3: DBBA; hydrogen bromide; acetic acid / dichloromethane / 25 °C / |Large scale 4: sodium acetate / water; acetonitrile / 3 h / 40 °C / |Large scale 5: sodium hydroxide / water / 1.5 h / 40 °C / |Large scale 6: 2-chloro-4,6-dimethoxy-[1,3,5]triazine; 4-methylmorpholine N-oxide / N,N-dimethyl-formamide / 1.5 h / 25 °C / |Large scale View Scheme

1: hydrogen; 5 palladium on charcoal / dichloromethane / 3.5 h / 3345.86 Torr / |Inert atmosphere; |Autoclave; |Large scale 2: 2,2,6,6-tetramethyl-1-piperidinyloxy, free radical; potassium bromide; sodium hypochlorite; sodium hydrogencarbonate / dichloromethane; water / -10 - 20 °C / pH 9.5 / |Large scale 3: DBBA; hydrogen bromide; acetic acid / dichloromethane / 25 °C / |Large scale 4: sodium acetate / water; acetonitrile / 3 h / 40 °C / |Large scale 5: sodium hydroxide / water / 1.5 h / 40 °C / |Large scale View Scheme

sulfuric acid; mercury(II) diacetate in acetic acid

sulfuric acid; mercury(II) diacetate in water 2 h; Heating;

1: hydrogen; 5 palladium on charcoal / dichloromethane / 3.5 h / 3345.86 Torr / |Inert atmosphere; |Autoclave; |Large scale 2: 2,2,6,6-tetramethyl-1-piperidinyloxy, free radical; potassium bromide; sodium hypochlorite; sodium hydrogencarbonate / dichloromethane; water / -10 - 20 °C / pH 9.5 / |Large scale 3: DBBA; hydrogen bromide; acetic acid / dichloromethane / 25 °C / |Large scale 4: sodium acetate / water; acetonitrile / 3 h / 40 °C / |Large scale 5: sodium hydroxide / water / 1.5 h / 40 °C / |Large scale 6: 2-chloro-4,6-dimethoxy-[1,3,5]triazine; 4-methylmorpholine N-oxide / N,N-dimethyl-formamide / 1.5 h / 25 °C / |Large scale 7: ethanol / 3 h / |Reflux; |Large scale View Scheme

1: 2.60 g / H2 / 5percent palladium-on-charcoal / ethanol / 12 h / 2585.7 Torr 2: triethylamine / diethyl ether / 4 h / 0 - 20 °C View Scheme

1: 100 percent / H2 / Pd/C / methanol / 12 h / 2327.17 - 2585.74 Torr 2: 63 percent / aq. CrO3; sulfuric acid / acetone / 0 - 20 °C 3: oxalyl chloride / CH2Cl2 / 1 h / Heating 4: diethyl ether / 1.17 h / cooling 5: 2 g / aq. HCl / diethyl ether / 1.5 h / Heating View Scheme

1: 2.60 g / H2 / 5percent palladium-on-charcoal / ethanol / 12 h / 2585.7 Torr 2: triethylamine / diethyl ether / 4 h / 0 - 20 °C 3: 1.) NaH / 1.) THF, 0 deg C -> room temperature, 2.) room temperature, 12 h; reflux, 6 h 4: 1.) sodium methoxide / 1.) anhydrous methanol, nitrogen atmosphere, 0.5 h, 2.) anhydrous dimethylformamide, mild warming, 12 h 5: 2.33 g / 1N sodium hydroxide / 18 h / Ambient temperature View Scheme