1: 69 percent / benzyltriethylammonium chloride / H2O; CHCl3 / 2 h / Heating 2: 92 percent / aq. Ba(OH)2 / dioxane / 15 h / 115 °C View Scheme

18-crown-6 ether; potassium carbonate in acetone Alkylation; Heating;

1: lithium bromide / tetrahydrofuran / Heating 2: 23 percent / K2CO3; 18-crown-6 / tetrahydrofuran / 12 h / Heating View Scheme

1: lithium bromide / tetrahydrofuran / Heating 2: 23 percent / K2CO3; 18-crown-6 / tetrahydrofuran / 12 h / Heating 3: (dimethylamino)pyridine; triethylamine / tetrahydrofuran / 3 h / 20 °C 4: lithium bromide / tetrahydrofuran / Heating View Scheme

1: 93 percent / 2-methoxy-ethanol / 17 h / 24 °C 2: 97 percent / KOH / ethanol / 18 h / Heating 3: 96 percent / HCl / 16.5 h View Scheme

lithium bromide in tetrahydrofuran Heating;

1: 69 percent / BzNEt3Cl / CHCl3; H2O 2: 92 percent / Ba(OH)2 / dioxane; H2O 3: diethyl ether 4: 99 percent / 60percent HClO4 / H2O; acetic acid 5: 97 percent / H2 / Pd/C (5percent) / ethyl acetate; ethanol 6: CH3ONa / methanol View Scheme

1.1: 69 percent / benzyltriethylammonium chloride / H2O; CHCl3 / 2 h / Heating 2.1: 92 percent / aq. Ba(OH)2 / dioxane / 15 h / 115 °C 3.1: 99 percent / AcOH; 60 percent aq. HClO4 / 0.08 h / 35 °C 4.1: 97 percent / H2 / 5 percent Pd/C / ethanol 5.1: MeONa / methanol / 0.33 h / 60 °C 5.2: 20 percent / NaBH4 / methanol / 4 h / 60 °C 6.1: 76 percent / 1N NaOH / 3 h / 45 °C View Scheme

1: 69 percent / BzNEt3Cl / CHCl3; H2O 2: 92 percent / Ba(OH)2 / dioxane; H2O 3: diethyl ether 4: 99 percent / 60percent HClO4 / H2O; acetic acid 5: 97 percent / H2 / Pd/C (5percent) / ethyl acetate; ethanol 6: CH3ONa / methanol 7: NaBH4 / methanol View Scheme