hydrogen; nickel in 2-methoxy-ethanol T=80°C; P=1520 - 2280 Torr; 4 h;

1: 17 percent / EtONa / 10 h / 110 - 120 °C 2: 1.) conc. HCl, NaNO2, 2.) Na2CO3, NaOAc / 1.) H2O, 0 deg C, 2.) H2O, EtOH, RT, 30 min 3: 49 percent / 1 h / 130 °C 4: 69 percent / H2 / Raney nickel / 2-methoxy-ethanol / 4 h / 80 °C / 1520 - 2280 Torr View Scheme

1: 1.) conc. HCl, NaNO2, 2.) Na2CO3, NaOAc / 1.) H2O, 0 deg C, 2.) H2O, EtOH, RT, 30 min 2: 49 percent / 1 h / 130 °C 3: 69 percent / H2 / Raney nickel / 2-methoxy-ethanol / 4 h / 80 °C / 1520 - 2280 Torr View Scheme