1: 98 percent / K2CO3 / acetone / 1.5 h / Heating 2: 55 percent / dimethylformamide / 2 h / Heating 3: NaOH, water / methanol / 84 h / Heating View Scheme

1: 98 percent / K2CO3 / acetone / 1.5 h / Heating 2: 1.) Br2, 2.) silver trifluoroacetate in benzene / 1.) CCl4, a) irrad., reflux, 5.75 h, b) reflux, 1.5 h, 2.) CCl4, benzene, 2.5 h 3: lithium methoxide / dimethylformamide / 14 h / 90 °C 4: 92 percent / conc. HCl, H2 / 10 percent Pd/C / acetic acid 5: 98 percent / Br2 / CH2Cl2 6: 68 percent / copper bronze / 2 h / 210 °C 7: 96 percent / LiAlH4 / diethyl ether / 1 h / Heating 8: 88 percent / pyridinium chlorochromate / CH2Cl2 / 0.5 h / Ambient temperature 9: 96 percent / butyllithium / hexane; tetrahydrofuran / 0.5 h / Ambient temperature 10: 92 percent / hexamethylphosphoric acid triamide / 2 h / 160 °C View Scheme

potassium carbonate in acetone 1.5 h; Heating;

1: 98 percent / K2CO3 / acetone / 1.5 h / Heating 2: 55 percent / dimethylformamide / 2 h / Heating View Scheme