1: Na, CH3OH / 0.08 h 2: 61 percent / xylene / 168 h / Heating 3: 1.) SnCl4 / 1.) CH2Cl2, -78 deg C, 15 min 2.) 20 h, room temp. 4: LiAlH4 / tetrahydrofuran / 24 h / Ambient temperature 5: pyridinium chlorochromate / CH2Cl2 / 3 h / Ambient temperature View Scheme

Multi-step reaction with 3 steps 1: Na, CH3OH / 0.08 h2: 61 percent / xylene / 168 h / Heating3: 1.) SnCl4 / 1.) CH2Cl2, -78 deg C, 15 min 2.) 20 h, room temp.  

With  methanol; sodium 0.0833333 h;  Yield given;   

With  sodium iodide in  acetic acid 3 h;  Heating;   

With  sodium iodide in  acetic acid 3 h;  Heating;