sodium hydroxide in water T=20 - 35°C; 16 h; Product distribution / selectivity;

in dimethyl sulfoxide T=25 - 40°C; 7 h;

1: H2 / 10percent Pd-C / methanol / 760 Torr / Ambient temperature 2: 1.)47percent HBr, NaNO2, 2.)Cu2O / 1.)MeOH, H2O, 5 deg C, 20 min., 2.)40 deg C View Scheme

1: H2 / 10percent Pd-C / methanol / 760 Torr / Ambient temperature 2: 1.)47percent HBr, NaNO2, 2.)Cu2O / 1.)MeOH, H2O, 5 deg C, 20 min., 2.)40 deg C 3: 53 percent / NaOAc / ethanol / Heating View Scheme

1: H2 / 10percent Pd-C / methanol / 760 Torr / Ambient temperature 2: 1.)47percent HBr, NaNO2, 2.)Cu2O / 1.)MeOH, H2O, 5 deg C, 20 min., 2.)40 deg C 3: 53 percent / NaOAc / ethanol / Heating 4: 2N HCl / 6 h / Heating 5: 12.2 g / 11percent ethanolic HCl / 1 h / Ambient temperature View Scheme

1: H2 / 10percent Pd-C / methanol / 760 Torr / Ambient temperature 2: 1.)47percent HBr, NaNO2, 2.)Cu2O / 1.)MeOH, H2O, 5 deg C, 20 min., 2.)40 deg C 3: 53 percent / NaOAc / ethanol / Heating 4: 2N HCl / 6 h / Heating View Scheme

1: H2 / 10percent Pd-C / methanol / 760 Torr / Ambient temperature 2: 1.)47percent HBr, NaNO2, 2.)Cu2O / 1.)MeOH, H2O, 5 deg C, 20 min., 2.)40 deg C 3: 70percent m-chloroperbenzoic acid / methanol / Heating 4: 80 °C 5: NaOAc / ethanol / Heating 6: 3N HCl / Heating View Scheme

hydrogen; Raney nickel in methanol T=-15 - 30°C; P=2206.72 - 2942.29 Torr; Product distribution / selectivity;