1: 96 percent / H2 / 10percent Pd/C / ethyl acetate / 1034.3 Torr 2: 62 percent / NaNO2, HF, pyridine / 2 h / 65 °C 3: 100 percent / n-bromosuccinimide (NBS), (PhCO2)2 / CCl4 / 4 h / Heating 4: 99 percent / HCO2Na / ethanol; H2O / 2 h / Heating 5: 71 percent / Jones reagent / acetone / 2 h / 10 - 15 °C 6: COCl2 / dimethylformamide; CH2Cl2 / 1 h 7: 96 percent / Et3N / tetrahydrofuran / 0.5 h / 0 - 20 °C 8: 1.) NaH / 1.) THF, 55-60 deg C, 45 min, 2.) THF, RT, 30 min 9: 98 percent / HCO2H / H2O / 1.5 h View Scheme

Multi-step reaction with 8 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 °C6: COCl2 / dimethylformamide; CH2Cl2 / 1 h7: 96 percent / Et3N / tetrahydrofuran / 0.5 h / 0 - 20 °C8: 1.) NaH / 1.) THF, 55-60 deg C, 45 min, 2.) THF, RT, 30 min  

Multi-step reaction with 4 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 / Heating  

Multi-step reaction with 3 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 / Heating  

Multi-step reaction with 2 steps 1: 96 percent / H2 / 10percent Pd/C / ethyl acetate / 1034.3 Torr2: 62 percent / NaNO2, HF, pyridine / 2 h / 65 °C  

Multi-step reaction with 7 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 °C6: COCl2 / dimethylformamide; CH2Cl2 / 1 h7: 96 percent / Et3N / tetrahydrofuran / 0.5 h / 0 - 20 °C  

With  hydrogen; palladium on activated charcoal in  ethyl acetate P=1034.3 Torr;   

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