in dichloromethane

sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride in hexane; water Ambient temperature; Further byproducts given;

diethyl ether

1: 10.83 g / H2O; dioxane / 10 h / Heating 2: 63 percent / NaH / tetrahydrofuran / 0.5 h / Heating 3: NaBH4 / methanol; tetrahydrofuran / 2 h / 4 - 7 °C 4: BF3*Et2O; MgSO4 / CH2Cl2 / 5 h / 20 °C 5: H2 / Pd(OH)2/C / acetic acid / 3 h / 20 °C 6: Na/Hg; Na3PO4 / methanol / 2 h / 20 °C 7: 86 percent / LiAlH4 / tetrahydrofuran / 2 h / Heating View Scheme

1: 10.83 g / H2O; dioxane / 10 h / Heating 2: 63 percent / NaH / tetrahydrofuran / 0.5 h / Heating 3: NaBH4 / methanol; tetrahydrofuran / 2 h / 4 - 7 °C 4: BF3*Et2O; MgSO4 / CH2Cl2 / 5 h / 20 °C 5: H2 / Pd(OH)2/C / acetic acid / 3 h / 20 °C 6: Na/Hg; Na3PO4 / methanol / 2 h / 20 °C 7: 92 percent / LiAlH4 / tetrahydrofuran / 2 h / Heating View Scheme