1: 95 percent / 20percent aq. KOH / ethanol / 48 h / Heating 2: thionyl chloride (SOCl2) / 1 h / Heating 3: AlCl3 / CH2Cl2 / 0.33 h / 0 °C 4: NaBH4 / CH2Cl2; methanol / 2 h / Ambient temperature 5: p-toluenesulfonic acid / toluene / 3 h / Heating 6: 32 percent / AgNO2, NaNO2, I2 / acetonitrile / 48 h / Ambient temperature 7: hydrazine monohydrate / Pd/C / tetrahydrofuran / 1 h / 0 °C View Scheme

1: 95 percent / 20percent aq. KOH / ethanol / 48 h / Heating 2: thionyl chloride (SOCl2) / 1 h / Heating 3: AlCl3 / CH2Cl2 / 0.33 h / 0 °C 4: 16 percent / ammonium nitrate, trifluoroacetic anhydride / acetonitrile / Ambient temperature 5: NaBH4 / CH2Cl2; methanol / 2 h / Ambient temperature 6: p-toluenesulfonic acid / toluene / 3 h / Heating 7: 56 percent / dichlorodicyanobenzoquinone (DDQ) / toluene / 2 h / Heating View Scheme

1: 95 percent / 20percent aq. KOH / ethanol / 48 h / Heating 2: thionyl chloride (SOCl2) / 1 h / Heating 3: AlCl3 / CH2Cl2 / 0.33 h / 0 °C 4: NaBH4 / CH2Cl2; methanol / 2 h / Ambient temperature 5: p-toluenesulfonic acid / toluene / 3 h / Heating 6: 32 percent / AgNO2, NaNO2, I2 / acetonitrile / 48 h / Ambient temperature View Scheme

1: 95 percent / 20percent aq. KOH / ethanol / 48 h / Heating 2: thionyl chloride (SOCl2) / 1 h / Heating 3: AlCl3 / CH2Cl2 / 0.33 h / 0 °C 4: NaBH4 / CH2Cl2; methanol / 2 h / Ambient temperature 5: p-toluenesulfonic acid / toluene / 3 h / Heating View Scheme

1: 95 percent / 20percent aq. KOH / ethanol / 48 h / Heating 2: thionyl chloride (SOCl2) / 1 h / Heating 3: AlCl3 / CH2Cl2 / 0.33 h / 0 °C 4: 25 percent / ammonium nitrate, trifluoroacetic anhydride / acetonitrile / Ambient temperature 5: NaBH4 / CH2Cl2; methanol / 2 h / Ambient temperature 6: p-toluenesulfonic acid / toluene / 3 h / Heating 7: 56 percent / dichlorodicyanobenzoquinone (DDQ) / toluene / 2 h / Heating View Scheme

1: 95 percent / 20percent aq. KOH / ethanol / 48 h / Heating 2: thionyl chloride (SOCl2) / 1 h / Heating 3: AlCl3 / CH2Cl2 / 0.33 h / 0 °C 4: NaBH4 / CH2Cl2; methanol / 2 h / Ambient temperature 5: p-toluenesulfonic acid / toluene / 3 h / Heating 6: 32 percent / AgNO2, NaNO2, I2 / acetonitrile / 48 h / Ambient temperature 7: 94 percent / hydrazine monohydrate / Raney Ni / ethanol / 2 h / Heating View Scheme

1: 95 percent / 20percent aq. KOH / ethanol / 48 h / Heating 2: thionyl chloride (SOCl2) / 1 h / Heating 3: AlCl3 / CH2Cl2 / 0.33 h / 0 °C 4: 16 percent / ammonium nitrate, trifluoroacetic anhydride / acetonitrile / Ambient temperature 5: NaBH4 / CH2Cl2; methanol / 2 h / Ambient temperature 6: p-toluenesulfonic acid / toluene / 3 h / Heating 7: 56 percent / dichlorodicyanobenzoquinone (DDQ) / toluene / 2 h / Heating 8: 95 percent / hydrazine monohydrate / Raney Ni / ethanol / 2 h / Heating View Scheme

potassium hydroxide in ethanol 48 h; Heating;

1: 95 percent / 20percent aq. KOH / ethanol / 48 h / Heating 2: thionyl chloride (SOCl2) / 1 h / Heating 3: AlCl3 / CH2Cl2 / 0.33 h / 0 °C 4: 25 percent / ammonium nitrate, trifluoroacetic anhydride / acetonitrile / Ambient temperature 5: NaBH4 / CH2Cl2; methanol / 2 h / Ambient temperature 6: p-toluenesulfonic acid / toluene / 3 h / Heating 7: 56 percent / dichlorodicyanobenzoquinone (DDQ) / toluene / 2 h / Heating 8: 96 percent / hydrazine monohydrate / Raney Ni / ethanol / 2 h / Heating View Scheme

1: 95 percent / 20percent aq. KOH / ethanol / 48 h / Heating 2: thionyl chloride (SOCl2) / 1 h / Heating 3: AlCl3 / CH2Cl2 / 0.33 h / 0 °C View Scheme