hydrogenchloride in methanol 4 h;

ruthenium(IV) oxide in tetrachloromethane T=0 - 5°C; electrolyse: aq. buffered NaCl (pH 4), platinum electrodes, 20 mA/cm2, electricity: 6.7 F/mol;

1: 78 percent / conc. HCl / methanol / 4 h 2: 1.) H2, 2.) PBr3 / 1.) NIP-2 / 2.) ether, reflux, 4 h 3: 1.) EtMgBr, 2.) CuCN, HMPT / 1.) THF, RT, 2 h, 2.) THF, 3 h 4: 79 percent / conc. H2SO4 / CCl4 / 10 h View Scheme

1: 78 percent / conc. HCl / methanol / 4 h 2: H2 / NIP-2 View Scheme

ruthenium(IV) oxide in tetrachloromethane T=0 - 5°C; electrolyse: aq. buffered NaCl (pH 4), platinum electrodes, 20 mA/cm2, electricity: 6.7 F/mol;

1: 78 percent / conc. HCl / methanol / 4 h 2: H2 / NIP-2 View Scheme

1: 78 percent / conc. HCl / methanol / 4 h 2: 1.) H2, 2.) PBr3 / 1.) NIP-2 / 2.) ether, reflux, 4 h 3: 1.) EtMgBr, 2.) CuCN, HMPT / 1.) THF, RT, 2 h, 2.) THF, 3 h 4: 79 percent / conc. H2SO4 / CCl4 / 10 h 5: LiAlH4 / bis-(2-methoxy-ethyl) ether; tetrahydrofuran / 20 h / 145 - 150 °C 6: 88 percent / pyridine / 24 h / Ambient temperature View Scheme

1: 78 percent / conc. HCl / methanol / 4 h 2: 1.) H2, 2.) PBr3 / 1.) NIP-2 / 2.) ether, reflux, 4 h 3: 1.) EtMgBr, 2.) CuCN, HMPT / 1.) THF, RT, 2 h, 2.) THF, 3 h 4: 79 percent / conc. H2SO4 / CCl4 / 10 h 5: LiAlH4 / bis-(2-methoxy-ethyl) ether; tetrahydrofuran / 20 h / 145 - 150 °C View Scheme