sulfuric acid

1: hydrochloric acid / methanol; H2O / 20 h / Ambient temperature 2: sodium methoxide / 3 h / Heating 3: acid resin (Dowex 50W-XH) / methanol / 12 h / Heating 4: pyridine / CH2Cl2; pyridine / 0.25 h / -30 °C 5: sodium azide / dimethylformamide / 24 h / 50 °C 6: 80 percent / sodium metoxide / methanol / 6 h / Ambient temperature 7: 81 percent / pyridine / 4 h / from 0 deg C to room temp. 8: 94 percent / pyridine / 4 h / Ambient temperature 9: 82 percent / sodium methoxide / dimethylformamide / 0.08 h / 50 °C 10: sodium methoxide / dimethylformamide / 3 h / 50 °C 11: hydrogen / palladium black / ethanol / 1 h 12: aq. sodium bicarbonate / diethyl ether / 2 h / Ambient temperature 13: 1.) 50percent aq. trifluoroacetic acid, 2.) sodium borohydride / 1.) room temp., 15 ethanol, min; 2.) water, room temp., 10 min 14: 70 percent / hydrogen / palladium black / acetic acid / 13 h View Scheme

formic acid; palladium on activated charcoal in methanol Product distribution;

1: methanol / 0.5percent HCl / Ambient temperature 2: sodium methoxide / Heating 3: methanol / Dowex 50W-X8 resin (H+ form) / Heating 4: pyridine / CH2Cl2 / 0.33 h / -20 °C 5: NaN3 / dimethylformamide / 48 h / 50 °C 6: methanol / sodium methylate / Ambient temperature 7: pyridine / 0 °C 8: pyridine / 4 h / Ambient temperature 9: sodium methoxyde / dimethylformamide / 5 h / 50 °C 11: H2O / CF3COOH / Ambient temperature 12: NaBH4 / ethanol; H2O 13: H2 / palladium hydroxide / ethanol View Scheme

acetic acid; periodic acid in water 0.416667 h; Ambient temperature;