1: thionyl chloride / 2 h / 100 °C 2: diethyl ether / Ambient temperature 3: AgNO3, NH4OH / dioxane; H2O / 16 h / Heating 4: aq. NaOH / 2-ethoxy-ethanol / 16 h / Heating View Scheme

1: With potassium hydroxide; ethanol; water 20 h; Heating / reflux; 2: With hydrogenchloride; water in ethanol

copper(l) iodide; copper; potassium carbonate; pyridine in water Ullmann-Goldberg condensation; 0.333333 h; ultrasound irradiation;

1: thionyl chloride / 2 h / 100 °C 2: diethyl ether / Ambient temperature 3: AgNO3, NH4OH / dioxane; H2O / 16 h / Heating 4: aq. NaOH / 2-ethoxy-ethanol / 16 h / Heating 5: thionyl chloride / 2 h / 100 °C 6: diethyl ether / Ambient temperature 7: AgNO3, NH4OH / dioxane / 16 h / Heating 8: aq. NaOH / 2-ethoxy-ethanol / 16 h / Heating View Scheme

sulfuric acid