1: 1) conc. aq. HCl, 2) Na2SO4 / 1) 1,2-dichloroethane, -2 deg C, 30 min, 2) 1,2-dichloroethane 2: 1) H2, 1,2-bis(2-hydroxyethylthio)ethane / 1) Raney-Ni (Degussa, type B 113 W), 2) Pd(OAc)2 / 1) methanol, 2h, room temp., ambient pressure, 2) methanol, 4h, 65 deg C 3: 90 percent / 1,2-epoxybutane / ethanol / 20 h / Heating View Scheme

1: 1) conc. aq. HCl, 2) Na2SO4 / 1) 1,2-dichloroethane, -2 deg C, 30 min, 2) 1,2-dichloroethane 2: 1) H2, 1,2-bis(2-hydroxyethylthio)ethane / 1) Raney-Ni (Degussa, type B 113 W), 2) Pd(OAc)2 / 1) methanol, 2h, room temp., ambient pressure, 2) methanol, 4h, 65 deg C 3: 90 percent / 1,2-epoxybutane / ethanol / 20 h / Heating View Scheme