1: With sodium tetrahydroborate in methanol T=0°C; 2: With sodium hydroxide in ethyl acetate

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