1: 96 percent / NaHCO3 / dimethylformamide / 8 h / 110 - 120 °C 2: 85 percent / NaH, ethanol / toluene / 2 h / Ambient temperature 3: 94 percent / chloranil / toluene / 1.5 h / Heating 4: 89 percent / 1N-NaOH / dioxane / 1 h / Heating 5: 92 percent / m-chloroperoxybenzoic acid / CHCl3 / 1 h / Ambient temperature; excess of reagent 6: 68 percent / triethylamine / acetonitrile / 0.5 h / Heating View Scheme

1: 61 percent / LiAlH4 / tetrahydrofuran 2: 61 percent / benzene / 4 h / Heating; removal of water View Scheme

lithium aluminium tetrahydride in tetrahydrofuran

diethyl ether