nitric acid; acetic acid

1: potassium carbonate; benzene 2: methanol. KOH-solution View Scheme

sodium methylate; copper 2) reflux, 18 h; Yield given. Multistep reaction;

1: acetic acid; aqueous nitric acid 2: palladium/charcoal; ethanol / Hydrogenation View Scheme

1: 1.) C2O2Cl2, 3.) SO2Cl2 2: 1.) Mg, 1,2-dibromotetrafluoroethane / 1) THF, 1 h; 2) THF, 50-60 deg C, 4-6 h 3: 1.) H2SO4, 2.) H2 / 2.) Pd/C / 1) EtOH, reflux, overnight; 2) EtOH, rt, 4 h View Scheme