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1: 30 percent / sodium hydroxide / H2O / 6 h / Heating 2: 1.) sodium hydride / 1.) DMF, 1 h, 0 deg C; 2.) DMF, 4 h, RT View Scheme

Heating;

1: 2) H2O / 1) dioxane, 120 deg C, 5 h, 2) dioxane, reflux, 1 h 2: 55.2 percent / Ac2O, azeotropic HBr in H2O / 4 h / 140 °C 3: 90.5 percent / p-TsOH / benzene / 6 h / Heating; azeotropic dist. View Scheme

1: 64.2 percent / p-TsOH / benzene / Heating; azeotropic dist. 2: 2) H2O / 1) dioxane, 120 deg C, 5 h, 2) dioxane, reflux, 1 h 3: 55.2 percent / Ac2O, azeotropic HBr in H2O / 4 h / 140 °C 4: 90.5 percent / p-TsOH / benzene / 6 h / Heating; azeotropic dist. View Scheme

1: 2.)water / 1.) dioxane, 5 h, reflux, 2.) 45 min, reflux 2: 55 percent / azeotropic hydrobromic acid / acetic anhydride 3: 90.5 percent / Heating View Scheme