hydrogen; nickel in ethanol P=760 Torr;

1: 90 percent / H2 / 10percent Pd/C / acetic acid / 6 h / 2585.7 Torr / Ambient temperature 2: 95 percent / PPA / 1 h / 120 °C 3: 82 percent / DIBAL-H / toluene / 2 h / -78 °C 4: 98 percent / POCl3 / triethylamine / 1.) RT, 3 h, 2.) reflux, 1 h 5: 1.) NaBH4, 2.) NaBH4, 3.) NH3, 4.) Li, 5.) Jones reagent View Scheme

1: 80 percent / AlCl3 / nitromethane / 2 h / 0 - 20 °C 2: 90 percent / H2 / 10percent Pd/C / acetic acid / 6 h / 2585.7 Torr / Ambient temperature 3: 95 percent / PPA / 1 h / 120 °C 4: 82 percent / DIBAL-H / toluene / 2 h / -78 °C 5: 98 percent / POCl3 / triethylamine / 1.) RT, 3 h, 2.) reflux, 1 h 6: 1.) NaBH4, 2.) NaBH4, 3.) NH3, 4.) Li, 5.) Jones reagent View Scheme

hydrogen; nickel

1: 1.) POCl3 / 1.) 10-20 deg C, 15 min., 2.) 110 deg C, 6 h 2: 74.6 percent / aq. NaOH / 7 h / 20 - 25 °C 3: 85 percent / H2 / Raney Ni / ethanol / 760 Torr View Scheme

1: 83.5 percent / KOH / ethanol; H2O / 14 h / 20 - 60 °C / 1.) 2 h, 20-25 deg C, 2.) 12 h, 60 deg C 2: 1.) POCl3 / 1.) 10-20 deg C, 15 min., 2.) 110 deg C, 6 h 3: 74.6 percent / aq. NaOH / 7 h / 20 - 25 °C 4: 85 percent / H2 / Raney Ni / ethanol / 760 Torr View Scheme

1: 74.6 percent / aq. NaOH / 7 h / 20 - 25 °C 2: 85 percent / H2 / Raney Ni / ethanol / 760 Torr View Scheme

1: 82 percent / DIBAL-H / toluene / 2 h / -78 °C 2: 98 percent / POCl3 / triethylamine / 1.) RT, 3 h, 2.) reflux, 1 h 3: 1.) NaBH4, 2.) NaBH4, 3.) NH3, 4.) Li, 5.) Jones reagent View Scheme

1: 95 percent / PPA / 1 h / 120 °C 2: 82 percent / DIBAL-H / toluene / 2 h / -78 °C 3: 98 percent / POCl3 / triethylamine / 1.) RT, 3 h, 2.) reflux, 1 h 4: 1.) NaBH4, 2.) NaBH4, 3.) NH3, 4.) Li, 5.) Jones reagent View Scheme

1: 98 percent / POCl3 / triethylamine / 1.) RT, 3 h, 2.) reflux, 1 h 2: 1.) NaBH4, 2.) NaBH4, 3.) NH3, 4.) Li, 5.) Jones reagent View Scheme