potassium hydroxide in ethanol 3 h; Heating;

1: 95 percent / MnO2 / dioxane / 5 h / Heating 2: 1.) NaH, DMSO / 1.) 70 deg C, 1 h, 2.) 50 deg C, 24 h 3: 1.) H2SO4, 2.) 1N aq. NaOH, 3.) H2 / 3.) 10percent Pd/C View Scheme

1: thionyl chloride / CH2Cl2 2: 53 percent / potassium iodide / dimethylsulfoxide / 12 h / 80 °C 3: 83 percent / aq. KOH / ethanol / 3 h / Heating View Scheme

1: 1.) NaH, DMSO / 1.) 70 deg C, 1 h, 2.) 50 deg C, 24 h 2: 1.) H2SO4, 2.) 1N aq. NaOH, 3.) H2 / 3.) 10percent Pd/C View Scheme