sulfuric acid in methanol T=20°C; 0.00833333 h;

hydrogenchloride

1.1: 68 percent / HCl; SnCl2*2H2O / H2O / 3 h / 50 °C 2.1: 79 percent / H2SO4; molecular sieves 4 Angstroem / toluene / 2 h / Heating 3.1: i-PrMgBr / tetrahydrofuran / 1 h / -10 °C 3.2: CuCN*2LiCl / tetrahydrofuran / 0.5 h 3.3: 68 percent / tetrahydrofuran / -10 - 20 °C 4.1: 71 percent / sulfuric acid / methanol / 0.01 h / 20 °C View Scheme

1.1: 79 percent / H2SO4; molecular sieves 4 Angstroem / toluene / 2 h / Heating 2.1: i-PrMgBr / tetrahydrofuran / 1 h / -10 °C 2.2: CuCN*2LiCl / tetrahydrofuran / 0.5 h 2.3: 68 percent / tetrahydrofuran / -10 - 20 °C 3.1: 71 percent / sulfuric acid / methanol / 0.01 h / 20 °C View Scheme

1.1: i-PrMgBr / tetrahydrofuran / 1 h / -10 °C 1.2: CuCN*2LiCl / tetrahydrofuran / 0.5 h 1.3: 68 percent / tetrahydrofuran / -10 - 20 °C 2.1: 71 percent / sulfuric acid / methanol / 0.01 h / 20 °C View Scheme

hydrogenchloride

1: sodium nitrate; sulfuric acid / 0.17 h / 0 °C 2: palladium 10 on activated carbon; hydrogen / ethanol / 3.5 h / 20 °C / 1965.21 Torr View Scheme