1: 80 percent / diethylamine; triphenylphosphine; copper(I) iodide / palladium chloride / 20 °C 2: 100 percent / H2 / Pd/C / methanol / 12 h / 2327.17 - 2585.74 Torr 3: 63 percent / aq. CrO3; sulfuric acid / acetone / 0 - 20 °C 4: oxalyl chloride / CH2Cl2 / 1 h / Heating 5: diethyl ether / 1.17 h / cooling 6: 2 g / aq. HCl / diethyl ether / 1.5 h / Heating View Scheme

1: 100 percent / H2 / Pd/C / methanol / 12 h / 2327.17 - 2585.74 Torr 2: 63 percent / aq. CrO3; sulfuric acid / acetone / 0 - 20 °C 3: oxalyl chloride / CH2Cl2 / 1 h / Heating 4: diethyl ether / 1.17 h / cooling 5: 2 g / aq. HCl / diethyl ether / 1.5 h / Heating View Scheme

1: 63 percent / aq. CrO3; sulfuric acid / acetone / 0 - 20 °C 2: oxalyl chloride / CH2Cl2 / 1 h / Heating 3: diethyl ether / 1.17 h / cooling 4: 2 g / aq. HCl / diethyl ether / 1.5 h / Heating View Scheme

1: diethyl ether / 1.17 h / cooling 2: 2 g / aq. HCl / diethyl ether / 1.5 h / Heating View Scheme

1: oxalyl chloride / CH2Cl2 / 1 h / Heating 2: diethyl ether / 1.17 h / cooling 3: 2 g / aq. HCl / diethyl ether / 1.5 h / Heating View Scheme