hydrogenchloride

2: KOH / aq. ethanol / Heating 3: BCl3 View Scheme

1: KOH / aq. ethanol / Heating 2: BCl3 View Scheme

1: Zn / acetic acid 3: KOH / aq. ethanol / Heating 4: BCl3 View Scheme

1: HCl, TiCl4 / CH2Cl2 / 12 h / 0 - 25 °C 2: Zn / acetic acid 4: KOH / aq. ethanol / Heating 5: BCl3 View Scheme

2: HCl, TiCl4 / CH2Cl2 / 12 h / 0 - 25 °C 3: Zn / acetic acid 5: KOH / aq. ethanol / Heating 6: BCl3 View Scheme

1: 36.9 g / phosphoryl chloride / 1.5 h / Ambient temperature 2: 1.) m-chloroperbenzoic acid, 2.) aqueous potassium hydroxide / 1.) dichloromethane, room temperarure, 1.5 h, 2.) methanol, 0 deg C, 1 h 3: 59 percent / potassium carbonate, cooper(II) oxide / pyridine / 15 h / 140 °C 4: 90 percent / hydrogen chloride, titanium(IV) chloride / CH2Cl2 / 12 h / Ambient temperature 5: 620 mg / zinc, glacial acetic acid / 1 h 6: 518 mg / potassium carbonate / acetone / 23 h / Heating 7: 373 mg / potassium hydroxide / ethanol / 2 h / Heating 8: 247 mg / boron trichloride / CH2Cl2 / 1.) 0 deg C, 1 h, 2.) room temperature, 2 h View Scheme

1: 1.) m-chloroperbenzoic acid, 2.) aqueous potassium hydroxide / 1.) dichloromethane, room temperarure, 1.5 h, 2.) methanol, 0 deg C, 1 h 2: 59 percent / potassium carbonate, cooper(II) oxide / pyridine / 15 h / 140 °C 3: 90 percent / hydrogen chloride, titanium(IV) chloride / CH2Cl2 / 12 h / Ambient temperature 4: 620 mg / zinc, glacial acetic acid / 1 h 5: 518 mg / potassium carbonate / acetone / 23 h / Heating 6: 373 mg / potassium hydroxide / ethanol / 2 h / Heating 7: 247 mg / boron trichloride / CH2Cl2 / 1.) 0 deg C, 1 h, 2.) room temperature, 2 h View Scheme

1: 59 percent / potassium carbonate, cooper(II) oxide / pyridine / 15 h / 140 °C 2: 90 percent / hydrogen chloride, titanium(IV) chloride / CH2Cl2 / 12 h / Ambient temperature 3: 620 mg / zinc, glacial acetic acid / 1 h 4: 518 mg / potassium carbonate / acetone / 23 h / Heating 5: 373 mg / potassium hydroxide / ethanol / 2 h / Heating 6: 247 mg / boron trichloride / CH2Cl2 / 1.) 0 deg C, 1 h, 2.) room temperature, 2 h View Scheme

1: 59 percent / potassium carbonate, cooper(II) oxide / pyridine / 15 h / 140 °C 2: 90 percent / hydrogen chloride, titanium(IV) chloride / CH2Cl2 / 12 h / Ambient temperature 3: 620 mg / zinc, glacial acetic acid / 1 h 4: 518 mg / potassium carbonate / acetone / 23 h / Heating 5: 373 mg / potassium hydroxide / ethanol / 2 h / Heating 6: 247 mg / boron trichloride / CH2Cl2 / 1.) 0 deg C, 1 h, 2.) room temperature, 2 h View Scheme