1: 90 percent / iron, concentrated hydrochloric acid / methanol / 0.17 h 2: 46 percent / bis-(2-methoxy-ethyl) ether / 3 h / 130 - 140 °C View Scheme

1: 71 percent / hydrochloric acid, iron / methanol; dioxane / 0.5 h / Heating 2: 1.) sodium nitrite, sulfuric acid, 2.) potassium iodide, aq. sulfuric acid / 1.) acetic acid, 40 deg C, 30 min, 2.) RT, 60 min View Scheme

1: 82 percent / dimethylformamide / 2 h / 140 - 150 °C 2: 71 percent / hydrochloric acid, iron / methanol; dioxane / 0.5 h / Heating 3: 1.) sodium nitrite, sulfuric acid, 2.) potassium iodide, aq. sulfuric acid / 1.) acetic acid, 40 deg C, 30 min, 2.) RT, 60 min View Scheme

sulfuric acid; potassium iodide; sodium nitrite 1.) acetic acid, 40 deg C, 30 min, 2.) RT, 60 min; Yield given. Multistep reaction;