NiO2; sodium hydroxide in water T=25°C; 12 h;

sodium methylate in methanol T=65°C; 12 h;

1: 57 percent / FeSO4, NH4OH 2: NaOEt / methanol / 16.5 h / Heating View Scheme

sulfuric acid; chromic acid

sulfuric acid

1: acetic acid; sodium acetate; bromine 2: aqueous H2SO4 View Scheme

1: H2SO4 / 24 h / 65 °C 2: 78 percent / 1,3-dibromo-5,5-dimethylhydantoin, (PhCO)2O2 / CCl4 / 5 h / Heating 3: 89 percent / H2SO4 / 16 h / Heating 4: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 30 min, 2.) THF, hexane, -78 deg C, 1 h 5: t-BuOK / 1,2-dimethoxy-ethane; toluene / 5 h / 25 °C 6: TiCl4, Et3N / CH2Cl2 / 1 h / 25 °C 7: benzene / 12 h / 25 °C 8: 79 percent / Et3N / toluene / 4 h / -10 °C 9: 1.) HBr, 2.) K2CO3 / 1.) CF3CH2OH, 80 deg C, 24 h, 2.) CF3CH2OH, 25 deg C, 1 h View Scheme