1: 84 percent / 40percent aq. NaOH / 0 °C 2: 34 percent / ethanol / 6 h / Heating 3: 74 percent / K2CO3 / benzene / 1.) reflux, 8 h, 2.) RT, 12 h 4: 95 percent / CuBr2 / 1.5 h / Heating 5: 89 percent / LiAlH4 / tetrahydrofuran / 1.5 h / Heating 6: 59 percent / CH2Cl2 / 24 h / Ambient temperature 7: LiAlH4 / tetrahydrofuran / 2 h / Heating View Scheme

1: 83 percent / POCl3 / toluene / 3 h / Heating 2: 84 percent / 40percent aq. NaOH / 0 °C 3: 34 percent / ethanol / 6 h / Heating 4: 74 percent / K2CO3 / benzene / 1.) reflux, 8 h, 2.) RT, 12 h 5: 95 percent / CuBr2 / 1.5 h / Heating 6: 89 percent / LiAlH4 / tetrahydrofuran / 1.5 h / Heating 7: 59 percent / CH2Cl2 / 24 h / Ambient temperature 8: LiAlH4 / tetrahydrofuran / 2 h / Heating View Scheme

lithium aluminium tetrahydride in tetrahydrofuran 2 h; Heating;

1: 59 percent / CH2Cl2 / 24 h / Ambient temperature 2: LiAlH4 / tetrahydrofuran / 2 h / Heating View Scheme

1: 65 percent / Na / ethanol / 1.5 h / Heating 2: 74 percent / K2CO3 / benzene / 1.) reflux, 8 h, 2.) RT, 12 h 3: 95 percent / CuBr2 / 1.5 h / Heating 4: 89 percent / LiAlH4 / tetrahydrofuran / 1.5 h / Heating 5: 59 percent / CH2Cl2 / 24 h / Ambient temperature 6: LiAlH4 / tetrahydrofuran / 2 h / Heating View Scheme

1: 74 percent / K2CO3 / benzene / 1.) reflux, 8 h, 2.) RT, 12 h 2: 95 percent / CuBr2 / 1.5 h / Heating 3: 89 percent / LiAlH4 / tetrahydrofuran / 1.5 h / Heating 4: 59 percent / CH2Cl2 / 24 h / Ambient temperature 5: LiAlH4 / tetrahydrofuran / 2 h / Heating View Scheme

1: 89 percent / LiAlH4 / tetrahydrofuran / 1.5 h / Heating 2: 59 percent / CH2Cl2 / 24 h / Ambient temperature 3: LiAlH4 / tetrahydrofuran / 2 h / Heating View Scheme

1: 95 percent / CuBr2 / 1.5 h / Heating 2: 89 percent / LiAlH4 / tetrahydrofuran / 1.5 h / Heating 3: 59 percent / CH2Cl2 / 24 h / Ambient temperature 4: LiAlH4 / tetrahydrofuran / 2 h / Heating View Scheme