1: 2) 2 N HCl / 1) acetonitrile, 13 h, reflux, 2) 1 h, reflux 2: 92 percent / p-toluenesulfonic acid / benzene / 12 h / Heating 3: H2, conc. NH3 / Raney-Ni / ethanol / 6 h / 105 - 110 °C / 44130.5 Torr 4: 1) conc. HCl, 2) 2 N NaOH / 1) 2 h, 2) 15 min 5: 3 percent / O2 / methyl acetate / 16 h / Ambient temperature View Scheme

1: 92 percent / p-toluenesulfonic acid / benzene / 12 h / Heating 2: H2, conc. NH3 / Raney-Ni / ethanol / 6 h / 105 - 110 °C / 44130.5 Torr 3: 1) conc. HCl, 2) 2 N NaOH / 1) 2 h, 2) 15 min 4: 3 percent / O2 / methyl acetate / 16 h / Ambient temperature View Scheme

1: H2, conc. NH3 / Raney-Ni / ethanol / 6 h / 105 - 110 °C / 44130.5 Torr 2: 1) conc. HCl, 2) 2 N NaOH / 1) 2 h, 2) 15 min 3: 3 percent / O2 / methyl acetate / 16 h / Ambient temperature View Scheme

1: benzene / Heating 2: 2) 2 N HCl / 1) acetonitrile, 13 h, reflux, 2) 1 h, reflux 3: 92 percent / p-toluenesulfonic acid / benzene / 12 h / Heating 4: H2, conc. NH3 / Raney-Ni / ethanol / 6 h / 105 - 110 °C / 44130.5 Torr 5: 1) conc. HCl, 2) 2 N NaOH / 1) 2 h, 2) 15 min 6: 3 percent / O2 / methyl acetate / 16 h / Ambient temperature View Scheme

oxygen in methyl acetate 16 h; Ambient temperature;

in water T=150 - 160°C; 1.5 h; Yield given. Yields of byproduct given;

in water T=150 - 160°C; 1.5 h; also with D-erythrose, D-glucose, or L-rhamnose; Product distribution;