alkali

PPA T=80°C; Friedel-Crafts reaction; 12 h;

alkaline permanganate

1: 91 percent / polyphosphoric acid / 2 h / 70 °C 2: 84 percent / potassium t-butoxide / 2-methyl-propan-2-ol; 1,2-dimethoxy-ethane / 50 h / 20 °C 3: 84 percent / n-butyl-lithium, diethylamine / hexane; tetrahydrofuran; hexamethylphosphoric acid triamide 4: 1.) di-isobutylaluminium hydride, 2.) aqueous acetic acid / 1.) toluene, -78 deg C, 2.5 h, 2.) room temperature, 30 min 5: 98 percent / m-hydrochloric acid / tetrahydrofuran / 12 h 6: 92 percent / aqueous potassium hydroxide / methanol / 24 h / 20 °C 7: 85 percent / lithium 1,1-dimethylethanethiolate / hexamethylphosphoric acid triamide / 2 h / 70 °C 8: 51 mg / H2 / 5percent Pd-C / ethyl acetate 9: 33 percent / sodium borohydride / methanol / 3 h View Scheme

1: P2O5/H3PO4 / 0.75 h / 60 °C 2: LDA / tetrahydrofuran / 0 °C 3: TsOH / dioxane; H2O / Heating View Scheme

1: 91 percent / polyphosphoric acid / 2 h / 70 °C 2: 96 percent / boron trichloride / CH2Cl2 / 2 h View Scheme

1.1: 70 percent / methane sulfonic acid / 6 h / 95 °C 2.1: diethyl oxalate; NaOMe / toluene / 0 - 20 °C 2.2: 54 percent / KOH; aq. H2O2 / methanol / 19 h 3.1: 96.7 percent / acetic anhydride / toluene / 1 h / Heating View Scheme

1: oxalyl chloride / DMF / benzene / 0.5 h / Ambient temperature 2: diethyl ether 3: Ag2O / 3 h / 60 °C 4: 96 percent / KOH / methanol; H2O / 3 h 5: 87 percent / polyphosphoric acid / 4 h / 100 - 110 °C View Scheme

1: 91 percent / polyphosphoric acid / 2 h / 70 °C 2: 84 percent / potassium t-butoxide / 2-methyl-propan-2-ol; 1,2-dimethoxy-ethane / 50 h / 20 °C 3: 84 percent / n-butyl-lithium, diethylamine / hexane; tetrahydrofuran; hexamethylphosphoric acid triamide 4: 1.) di-isobutylaluminium hydride, 2.) aqueous acetic acid / 1.) toluene, -78 deg C, 2.5 h, 2.) room temperature, 30 min 5: 98 percent / m-hydrochloric acid / tetrahydrofuran / 12 h 6: 92 percent / aqueous potassium hydroxide / methanol / 24 h / 20 °C 7: 85 percent / lithium 1,1-dimethylethanethiolate / hexamethylphosphoric acid triamide / 2 h / 70 °C 8: 51 mg / H2 / 5percent Pd-C / ethyl acetate View Scheme

1: 91 percent / polyphosphoric acid / 2 h / 70 °C 2: 84 percent / potassium t-butoxide / 2-methyl-propan-2-ol; 1,2-dimethoxy-ethane / 50 h / 20 °C 3: 84 percent / n-butyl-lithium, diethylamine / hexane; tetrahydrofuran; hexamethylphosphoric acid triamide 4: 1.) di-isobutylaluminium hydride, 2.) aqueous acetic acid / 1.) toluene, -78 deg C, 2.5 h, 2.) room temperature, 30 min 5: 98 percent / m-hydrochloric acid / tetrahydrofuran / 12 h 6: 92 percent / aqueous potassium hydroxide / methanol / 24 h / 20 °C 7: 85 percent / lithium 1,1-dimethylethanethiolate / hexamethylphosphoric acid triamide / 2 h / 70 °C 8: 51 mg / H2 / 5percent Pd-C / ethyl acetate 9: 7 percent / sodium borohydride / methanol / 3 h View Scheme