1: COCl2 / dimethylformamide; CH2Cl2 / 1 h 2: 96 percent / Et3N / tetrahydrofuran / 0.5 h / 0 - 20 °C 3: 1.) NaH / 1.) THF, 55-60 deg C, 45 min, 2.) THF, RT, 30 min 4: 98 percent / HCO2H / H2O / 1.5 h View Scheme

Multi-step reaction with 3 steps 1: COCl2 / dimethylformamide; CH2Cl2 / 1 h2: 96 percent / Et3N / tetrahydrofuran / 0.5 h / 0 - 20 °C3: 1.) NaH / 1.) THF, 55-60 deg C, 45 min, 2.) THF, RT, 30 min  

Multi-step reaction with 2 steps 1: COCl2 / dimethylformamide; CH2Cl2 / 1 h2: 96 percent / Et3N / tetrahydrofuran / 0.5 h / 0 - 20 °C  

With  jones reagent in  acetone T=10 - 15°C; 2 h;   

Multi-step reaction with 5 steps 1: 96 percent / H2 / 10percent Pd/C / ethyl acetate / 1034.3 Torr2: 62 percent / NaNO2, HF, pyridine / 2 h / 65 °C3: 100 percent / n-bromosuccinimide (NBS), (PhCO2)2 / CCl4 / 4 h / Heating4: 99 percent / HCO2Na / ethanol; H2O / 2 h / Heating5: 71 percent / Jones reagent / acetone / 2 h / 10 - 15 °C  

Multi-step reaction with 2 steps 1: 99 percent / HCO2Na / ethanol; H2O / 2 h / Heating2: 71 percent / Jones reagent / acetone / 2 h / 10 - 15 °C  

Multi-step reaction with 4 steps 1: 62 percent / NaNO2, HF, pyridine / 2 h / 65 °C2: 100 percent / n-bromosuccinimide (NBS), (PhCO2)2 / CCl4 / 4 h / Heating3: 99 percent / HCO2Na / ethanol; H2O / 2 h / Heating4: 71 percent / Jones reagent / acetone / 2 h / 10 - 15 °C  

Multi-step reaction with 3 steps 1: 100 percent / n-bromosuccinimide (NBS), (PhCO2)2 / CCl4 / 4 h / Heating2: 99 percent / HCO2Na / ethanol; H2O / 2 h / Heating3: 71 percent / Jones reagent / acetone / 2 h / 10 - 15 °C