sodium hydroxide in methanol Heating;

1: 69 percent / H2O / 48 h / 20 °C 2: 94 percent / K2CO3 / dimethylformamide / 2.5 h / 20 °C 3: 96 percent / 40 percent aq. NaOH / methanol / 4 h / Heating View Scheme

lithium aluminium tetrahydride in tetrahydrofuran; diethyl ether Heating;

1: 1.) H3PO4 / 1.) RT, 17 min, 2.) pyridine, RT 2: 88 percent / K2CO3 / methanol; acetone / 12 h / Ambient temperature 3: 60 percent / K2CO3 / acetone / 48 h / Heating 4: 79 percent / NBS / acetic acid; dioxane / 1 h / Ambient temperature 5: 84 percent / KOH / ethanol; H2O / 4 h / Heating 6: 89 percent / DCC, Et3N / CH2Cl2 7: 84 percent / PPE / 1,2-dichloro-ethane 8: 71 percent / NBS / CH2Cl2 / 0.5 h / Ambient temperature 9: 64 percent / BBr3 / CH2Cl2 / 5 h / Heating View Scheme