1: 4-dimethylamino-1-tert-butyldimethylsilyloxynaphthalene With tert.-butyl lithium in cyclohexane; pentane T=20°C; 72 h; 2: N,N-dimethyl-formamide With sulfuric acid; iodine in cyclohexane; pentane T=0 - 20°C; 3: With jones' reagent in acetone T=0°C; Jones' oxidation; 0.5 h; Further stages.;

1.1: NaH / tetrahydrofuran / 2 h / 0 °C 1.2: 1.27 g / tetrahydrofuran / 8 h / 0 - 20 °C 2.1: t-BuLi / cyclohexane; pentane / 72 h / 20 °C 2.2: I2 / cyclohexane; pentane / 0 - 20 °C 2.3: 40 percent / Jones' reagent / acetone / 0.5 h / 0 °C View Scheme

1: SnCl2, conc. HCl / acetic acid / 0.25 h / 100 °C 2: 6.1 g / FeCl3 / H2O 3: 1.) NaNO2, aq. H2SO4, 2.) KI / 1.) 10 deg C, 2.) water, 90 deg C View Scheme

1: 6.1 g / FeCl3 / H2O 2: 1.) NaNO2, aq. H2SO4, 2.) KI / 1.) 10 deg C, 2.) water, 90 deg C View Scheme

1: 75.1 percent / conc. H2SO4, NaNO3 / 1.) 20 deg C, 25 min, 2.) 40 deg C, 5 min 2: SnCl2, conc. HCl / acetic acid / 0.25 h / 100 °C 3: 6.1 g / FeCl3 / H2O 4: 1.) NaNO2, aq. H2SO4, 2.) KI / 1.) 10 deg C, 2.) water, 90 deg C View Scheme

Fremy’s salt

sulfuric acid; potassium iodide; sodium nitrite 1.) 10 deg C, 2.) water, 90 deg C; Yield given. Multistep reaction;

ammonium hydroxide; ammonium chloride; hydroxylammonium sulfate; copper(l) chloride 1.) ethanol, 2.) 75-80 deg C, 20 min; Yield given. Multistep reaction;