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

hydrogenchloride T=25°C; 2 h;