hydrogen; palladium on activated charcoal in methanol P=760 Torr; 0.666667 h; Ambient temperature;

1: H2 / 10percent Pd/C / 760 Torr / Ambient temperature 2: 95 percent / triethylamine / CH2Cl2 / 0.5 h / 10 - 15 °C 3: 84.6 percent / Dowex50W-8x ion-exchange resin (H+ form / aq. ethanol / 1.5 h / Heating 4: 264 g / benzoic acid / 0.5 h 5: 268 g / trimethylchlorosilane / CH2Cl2 / 0.75 h / Heating 6: 182 g / aq. NaOH / methanol / 0.5 h / 15 °C 7: 92 percent / Na, MeOH / 16 h / Heating 8: POCl3 / toluene / 1.5 h / Ambient temperature 9: sodium bis(2-methoxyethoxy)aluminum hydride / toluene / 1.5 h / 80 °C 10: 92.3 percent / H2 / 10percent Pd/C / methanol / 0.67 h / 760 Torr / Ambient temperature View Scheme

1: 84.6 percent / Dowex50W-8x ion-exchange resin (H+ form / aq. ethanol / 1.5 h / Heating 2: 264 g / benzoic acid / 0.5 h 3: 268 g / trimethylchlorosilane / CH2Cl2 / 0.75 h / Heating 4: 182 g / aq. NaOH / methanol / 0.5 h / 15 °C 5: 92 percent / Na, MeOH / 16 h / Heating 6: POCl3 / toluene / 1.5 h / Ambient temperature 7: sodium bis(2-methoxyethoxy)aluminum hydride / toluene / 1.5 h / 80 °C 8: 92.3 percent / H2 / 10percent Pd/C / methanol / 0.67 h / 760 Torr / Ambient temperature View Scheme

1: 95 percent / triethylamine / CH2Cl2 / 0.5 h / 10 - 15 °C 2: 84.6 percent / Dowex50W-8x ion-exchange resin (H+ form / aq. ethanol / 1.5 h / Heating 3: 264 g / benzoic acid / 0.5 h 4: 268 g / trimethylchlorosilane / CH2Cl2 / 0.75 h / Heating 5: 182 g / aq. NaOH / methanol / 0.5 h / 15 °C 6: 92 percent / Na, MeOH / 16 h / Heating 7: POCl3 / toluene / 1.5 h / Ambient temperature 8: sodium bis(2-methoxyethoxy)aluminum hydride / toluene / 1.5 h / 80 °C 9: 92.3 percent / H2 / 10percent Pd/C / methanol / 0.67 h / 760 Torr / Ambient temperature View Scheme

1: 264 g / benzoic acid / 0.5 h 2: 268 g / trimethylchlorosilane / CH2Cl2 / 0.75 h / Heating 3: 182 g / aq. NaOH / methanol / 0.5 h / 15 °C 4: 92 percent / Na, MeOH / 16 h / Heating 5: POCl3 / toluene / 1.5 h / Ambient temperature 6: sodium bis(2-methoxyethoxy)aluminum hydride / toluene / 1.5 h / 80 °C 7: 92.3 percent / H2 / 10percent Pd/C / methanol / 0.67 h / 760 Torr / Ambient temperature View Scheme

1: 92 percent / Na, MeOH / 16 h / Heating 2: POCl3 / toluene / 1.5 h / Ambient temperature 3: sodium bis(2-methoxyethoxy)aluminum hydride / toluene / 1.5 h / 80 °C 4: 92.3 percent / H2 / 10percent Pd/C / methanol / 0.67 h / 760 Torr / Ambient temperature View Scheme

1: 182 g / aq. NaOH / methanol / 0.5 h / 15 °C 2: 92 percent / Na, MeOH / 16 h / Heating 3: POCl3 / toluene / 1.5 h / Ambient temperature 4: sodium bis(2-methoxyethoxy)aluminum hydride / toluene / 1.5 h / 80 °C 5: 92.3 percent / H2 / 10percent Pd/C / methanol / 0.67 h / 760 Torr / Ambient temperature View Scheme

1: 268 g / trimethylchlorosilane / CH2Cl2 / 0.75 h / Heating 2: 182 g / aq. NaOH / methanol / 0.5 h / 15 °C 3: 92 percent / Na, MeOH / 16 h / Heating 4: POCl3 / toluene / 1.5 h / Ambient temperature 5: sodium bis(2-methoxyethoxy)aluminum hydride / toluene / 1.5 h / 80 °C 6: 92.3 percent / H2 / 10percent Pd/C / methanol / 0.67 h / 760 Torr / Ambient temperature View Scheme

1: POCl3 / toluene / 1.5 h / Ambient temperature 2: sodium bis(2-methoxyethoxy)aluminum hydride / toluene / 1.5 h / 80 °C 3: 92.3 percent / H2 / 10percent Pd/C / methanol / 0.67 h / 760 Torr / Ambient temperature View Scheme

1: 86 percent 2: 73 percent / 4 N NaOH / ethanol / 13 h / 80 °C 3: H2 / 5 percent Pd/C / ethanol / 6.5 h View Scheme