hydrogen; nickel in diethylene glycol dimethyl ether T=50°C; 16 h;

1: 1) NH4Cl, polyphosphoric acid, 2) H2O / 1) 160 deg C, 4 h, 2) r.t. 2: 95 percent / 40percent H2O2, acetic acid / 50 deg C, 3 h, then 20-25 deg C, 24 h 3: acetonitrile / 2 h / 80 °C 4: 95 percent / toluene / 2 h / 80 °C 5: 100 percent / H2 / Raney nickel / bis-(2-methoxy-ethyl) ether / 16 h / 50 °C View Scheme

1: 95 percent / 40percent H2O2, acetic acid / 50 deg C, 3 h, then 20-25 deg C, 24 h 2: acetonitrile / 2 h / 80 °C 3: 95 percent / toluene / 2 h / 80 °C 4: 100 percent / H2 / Raney nickel / bis-(2-methoxy-ethyl) ether / 16 h / 50 °C View Scheme

1: 90 percent / 40percent H2O2, acetic acid / 24 h / 55 - 60 °C / bath temperature 2: 8.96 g / conc. NH4OH, CuSO4*5H2O, NaCl / 5 h / 80 °C 3: 96 percent / 5percent aq. HCl / various solvent(s) / 1.5 h / 110 °C / bath temperature 4: acetonitrile / 2 h / 80 °C 5: 95 percent / toluene / 2 h / 80 °C 6: 100 percent / H2 / Raney nickel / bis-(2-methoxy-ethyl) ether / 16 h / 50 °C View Scheme

1: 95 percent / toluene / 2 h / 80 °C 2: 100 percent / H2 / Raney nickel / bis-(2-methoxy-ethyl) ether / 16 h / 50 °C View Scheme

1: acetonitrile / 2 h / 80 °C 2: 95 percent / toluene / 2 h / 80 °C 3: 100 percent / H2 / Raney nickel / bis-(2-methoxy-ethyl) ether / 16 h / 50 °C View Scheme

1: 90 percent / 40percent H2O2, acetic acid / 24 h / 55 - 60 °C / bath temperature 2: conc. NH4OH, CuSO4*5H2O, NaCl / 3 h / 60 °C 3: 96 percent / 5percent aq. HCl / various solvent(s) / 1.5 h / 110 °C / bath temperature 4: acetonitrile / 2 h / 80 °C 5: 95 percent / toluene / 2 h / 80 °C 6: 100 percent / H2 / Raney nickel / bis-(2-methoxy-ethyl) ether / 16 h / 50 °C View Scheme

1: 96 percent / 5percent aq. HCl / various solvent(s) / 1.5 h / 110 °C / bath temperature 2: acetonitrile / 2 h / 80 °C 3: 95 percent / toluene / 2 h / 80 °C 4: 100 percent / H2 / Raney nickel / bis-(2-methoxy-ethyl) ether / 16 h / 50 °C View Scheme

1: 8.96 g / conc. NH4OH, CuSO4*5H2O, NaCl / 5 h / 80 °C 2: 96 percent / 5percent aq. HCl / various solvent(s) / 1.5 h / 110 °C / bath temperature 3: acetonitrile / 2 h / 80 °C 4: 95 percent / toluene / 2 h / 80 °C 5: 100 percent / H2 / Raney nickel / bis-(2-methoxy-ethyl) ether / 16 h / 50 °C View Scheme

1: conc. NH4OH, CuSO4*5H2O, NaCl / 3 h / 60 °C 2: 96 percent / 5percent aq. HCl / various solvent(s) / 1.5 h / 110 °C / bath temperature 3: acetonitrile / 2 h / 80 °C 4: 95 percent / toluene / 2 h / 80 °C 5: 100 percent / H2 / Raney nickel / bis-(2-methoxy-ethyl) ether / 16 h / 50 °C View Scheme