hydrogenchloride; potassium carbonate in tetrahydrofuran; ethyl acetate; N,N-dimethyl-formamide

1: 41 percent / 70percent aq.HNO3, conc.H2SO4 / 2 h / Ambient temperature 2: (COCl)2 / CH2Cl2; dimethylformamide / 2 h / Ambient temperature 3: 1.) EtOH, Mg / 1.) toluene, 2.) toluene, RT, 2 h 4: p-TsOH / H2O / 0.83 h / Heating 5: 34 percent / Ac2O / 1 h / Heating 6: 23.3 g / ethanol / 0.5 h / Ambient temperature 7: 85 percent / K2CO3, 18-crown-6-ether / tetrahydrofuran / 8 h / 70 °C View Scheme

1: (COCl)2 / CH2Cl2; dimethylformamide / 2 h / Ambient temperature 2: 1.) EtOH, Mg / 1.) toluene, 2.) toluene, RT, 2 h 3: p-TsOH / H2O / 0.83 h / Heating 4: 34 percent / Ac2O / 1 h / Heating 5: 23.3 g / ethanol / 0.5 h / Ambient temperature 6: 85 percent / K2CO3, 18-crown-6-ether / tetrahydrofuran / 8 h / 70 °C View Scheme

1: 1.) EtOH, Mg / 1.) toluene, 2.) toluene, RT, 2 h 2: p-TsOH / H2O / 0.83 h / Heating 3: 34 percent / Ac2O / 1 h / Heating 4: 23.3 g / ethanol / 0.5 h / Ambient temperature 5: 85 percent / K2CO3, 18-crown-6-ether / tetrahydrofuran / 8 h / 70 °C View Scheme

1: 34 percent / Ac2O / 1 h / Heating 2: 23.3 g / ethanol / 0.5 h / Ambient temperature 3: 85 percent / K2CO3, 18-crown-6-ether / tetrahydrofuran / 8 h / 70 °C View Scheme

1: 90 percent / Fe, AcOH / 4.5 h / 90 °C 2: 87 percent / conc.HCl, AcOH / 2 h / Heating View Scheme