1: 72 percent / cc. nitric acid / 3 h / 0 - 2 °C 2: 93 percent / H2 / 10 percent Pd-C / ethanol / 6 h / 38000 Torr 3: 1.) cc. hydrochloric acid, 97 percent isoamyl nitrite; 2.) propylene oxide / 1.) abs. ethanol, 0 deg C, 10 min; 2.) 1,2-dichloroethane, reflux View Scheme

1: 93 percent / H2 / 10 percent Pd-C / ethanol / 6 h / 38000 Torr 2: 1.) cc. hydrochloric acid, 97 percent isoamyl nitrite; 2.) propylene oxide / 1.) abs. ethanol, 0 deg C, 10 min; 2.) 1,2-dichloroethane, reflux View Scheme

1: 85 percent / potassium permanganate / H2O / 1 h / 80 °C 2: 72 percent / cc. nitric acid / 3 h / 0 - 2 °C 3: 93 percent / H2 / 10 percent Pd-C / ethanol / 6 h / 38000 Torr 4: 1.) cc. hydrochloric acid, 97 percent isoamyl nitrite; 2.) propylene oxide / 1.) abs. ethanol, 0 deg C, 10 min; 2.) 1,2-dichloroethane, reflux View Scheme

1: isopentyl nitrite, trifluoroacetic acid / tetrahydrofuran / 1.) 0 deg C, 2.) room temperature, 2 h 2: 1,2-dichloro-ethane / 3 h / 50 - 55 °C View Scheme

methyloxirane in 1,2-dichloro-ethane Yield given;

in 1,2-dichloro-ethane T=50 - 55°C; 3 h; Yield given;

hydrogenchloride; methyloxirane; isopentyl nitrite 1.) abs. ethanol, 0 deg C, 10 min; 2.) 1,2-dichloroethane, reflux; Yield given. Multistep reaction;

hydrogen cation