1: NaBH4 2: (i) H2, Pd-C, (ii) aq. CrO3 View Scheme

1.1: iron; iron sulphate heptahydrate / water; ethanol / 4 h / |Inert atmosphere; |Reflux 2.1: sodium nitrite; hydrogenchloride; 1-phenylphosphoran / water / 0.25 h / 0 - 5 °C / |Inert atmosphere 2.2: 0 - 5 °C / |Inert atmosphere 3.1: dihydrogen peroxide; potassium hydroxide / methanol / 1.17 h / 65 °C 4.1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 3 h / |Inert atmosphere 5.1: dichloromethane / 0.5 h / |Inert atmosphere View Scheme

nitric acid; acetic acid T=0°C; 1.5 h; Inert atmosphere;