hydrogen; palladium on activated charcoal in methanol P=2205.2 Torr;

hydrogen; palladium on activated charcoal in methanol P=2250.2 Torr;

hydrogen; palladium dihydroxide in ethanol P=759.8 Torr; 16 h; Ambient temperature;

1: 97 percent / 4 h / 160 °C 2: acetyl chloride / 16 h / Heating 3: 85 percent / lithium aluminum hydride / diethyl ether / 3.5 h / Heating 4: 92 percent / thionyl chloride / CHCl3 / 2 h / Heating 5: 67 percent / tricaprylmethylammonium chloride / H2O / 48 h / 100 °C 6: 1.) acetyl chloride, 2.) water / 1.) RT, 48 h, 2.) 1 h 7: 62 percent / H2 / 10percent Pd-C / methanol / 2205.2 Torr View Scheme

1: acetyl chloride / 16 h / Heating 2: 85 percent / lithium aluminum hydride / diethyl ether / 3.5 h / Heating 3: 92 percent / thionyl chloride / CHCl3 / 2 h / Heating 4: 67 percent / tricaprylmethylammonium chloride / H2O / 48 h / 100 °C 5: 1.) acetyl chloride, 2.) water / 1.) RT, 48 h, 2.) 1 h 6: 62 percent / H2 / 10percent Pd-C / methanol / 2205.2 Torr View Scheme

1: 92 percent / thionyl chloride / CHCl3 / 2 h / Heating 2: 67 percent / tricaprylmethylammonium chloride / H2O / 48 h / 100 °C 3: 1.) acetyl chloride, 2.) water / 1.) RT, 48 h, 2.) 1 h 4: 62 percent / H2 / 10percent Pd-C / methanol / 2205.2 Torr View Scheme

1: 85 percent / lithium aluminum hydride / diethyl ether / 3.5 h / Heating 2: 92 percent / thionyl chloride / CHCl3 / 2 h / Heating 3: 67 percent / tricaprylmethylammonium chloride / H2O / 48 h / 100 °C 4: 1.) acetyl chloride, 2.) water / 1.) RT, 48 h, 2.) 1 h 5: 62 percent / H2 / 10percent Pd-C / methanol / 2205.2 Torr View Scheme

1: 1.) BH3*THF, 2.) HCl / 1.) reflux, 1 h, 2.) MeOH, reflux, 1 h 2: 53 percent / H2 / 10percent Pd/C / methanol / 2250.2 Torr View Scheme

Amberlite IRA 400 (OH(1-)); acetic acid

1: 97 percent / HCl, H2O / 24 h / 40 °C 2: 58 percent / H2 / 20percent Pd(OH)2/C / ethanol / 16 h / 759.8 Torr / Ambient temperature View Scheme