hydrogenchloride in acetic acid 4 h; Heating;

1: 1.) sodium hydride / 1.0 DMF, 2.) DMF, 16 h 2: 90 percent / aq. methanolic sodium hydroxide / 3 h / Heating 3: thionyl chloride 4: aluminum chloride / CH2Cl2 / 0.5 h / 0 °C 5: CH2Cl2; diethyl ether / 0.5 h 6: silver benzoate / 0.08 h / Heating 7: 71 percent / conc. hydrochloric acid / acetic acid / 4 h / Heating View Scheme

1: 60 percent / pyridine / 24 h / Ambient temperature 2: 1.) sodium hydride / 1.0 DMF, 2.) DMF, 16 h 3: 90 percent / aq. methanolic sodium hydroxide / 3 h / Heating 4: thionyl chloride 5: aluminum chloride / CH2Cl2 / 0.5 h / 0 °C 6: CH2Cl2; diethyl ether / 0.5 h 7: silver benzoate / 0.08 h / Heating 8: 71 percent / conc. hydrochloric acid / acetic acid / 4 h / Heating View Scheme

1: 1.) sodium hydride / 1.0 DMF, 2.) DMF, 16 h 2: 90 percent / aq. methanolic sodium hydroxide / 3 h / Heating 3: thionyl chloride 4: aluminum chloride / CH2Cl2 / 0.5 h / 0 °C 5: CH2Cl2; diethyl ether / 0.5 h 6: silver benzoate / 0.08 h / Heating 7: 71 percent / conc. hydrochloric acid / acetic acid / 4 h / Heating View Scheme

1: CH2Cl2; diethyl ether / 0.5 h 2: silver benzoate / 0.08 h / Heating 3: 71 percent / conc. hydrochloric acid / acetic acid / 4 h / Heating View Scheme

1: thionyl chloride 2: aluminum chloride / CH2Cl2 / 0.5 h / 0 °C 3: CH2Cl2; diethyl ether / 0.5 h 4: silver benzoate / 0.08 h / Heating 5: 71 percent / conc. hydrochloric acid / acetic acid / 4 h / Heating View Scheme

1: aluminum chloride / CH2Cl2 / 0.5 h / 0 °C 2: CH2Cl2; diethyl ether / 0.5 h 3: silver benzoate / 0.08 h / Heating 4: 71 percent / conc. hydrochloric acid / acetic acid / 4 h / Heating View Scheme

1: 90 percent / aq. methanolic sodium hydroxide / 3 h / Heating 2: thionyl chloride 3: aluminum chloride / CH2Cl2 / 0.5 h / 0 °C 4: CH2Cl2; diethyl ether / 0.5 h 5: silver benzoate / 0.08 h / Heating 6: 71 percent / conc. hydrochloric acid / acetic acid / 4 h / Heating View Scheme