1: 2.8 g / 50percent NaH / paraffin; benzene / 24 h / Heating 2: 2.3 g / K2CO3 / acetone / 5 h / Heating View Scheme

disodium hydrogenphosphate; sodium dihydrogenphosphate; Fremy’s salt; triisooctyl amine in dichloromethane; water Ambient temperature;

1: 1) LiPdCl4, NaOAc, 2) NEt3 / 1a) MeOH, 0 deg C, 10 min, 1b) r.t., 24 h, 2a) glac. acetic acid, CHCl3, 0 deg C, 10 min, 2b) r.t., 24-48 h 2: hexane; benzene / 2 h / Ambient temperature 3: NEt3 / tetrahydrofuran / 2 h / Ambient temperature 4: Li, NH3 / tetrahydrofuran / 0.25 h / -78 °C 5: 80 percent / Fremy's salt, Na2HPO4, NaH2PO4 / Adogen / CH2Cl2; H2O / Ambient temperature View Scheme

1: NEt3 / tetrahydrofuran / 2 h / Ambient temperature 2: Li, NH3 / tetrahydrofuran / 0.25 h / -78 °C 3: 80 percent / Fremy's salt, Na2HPO4, NaH2PO4 / Adogen / CH2Cl2; H2O / Ambient temperature View Scheme

1: hexane; benzene / 2 h / Ambient temperature 2: NEt3 / tetrahydrofuran / 2 h / Ambient temperature 3: Li, NH3 / tetrahydrofuran / 0.25 h / -78 °C 4: 80 percent / Fremy's salt, Na2HPO4, NaH2PO4 / Adogen / CH2Cl2; H2O / Ambient temperature View Scheme

jones reagent in acetone Yield given;

1: 14.8 g / formic acid / H2O / 2.5 h / 50 - 55 °C 2: Jones reagent / acetone View Scheme

1: 14.8 g / formic acid / H2O / 2.5 h / 50 - 55 °C 2: Jones reagent / acetone View Scheme

1: 1) n-BuLi / 1a) THF, 0 deg C, 10 min, 1b) to r.t., 2 h, 2) 0 deg C, 3 h View Scheme