Multi-step reaction with 9 steps
1: sodium nitrite, conc. H2SO4 / acetic acid; H2O / 0.17 h / 8 - 10 °C
2: 68percent HNO3 / H2O / 0.25 h / 45 °C
3: 58 percent / NaOH / H2O / 2 h / 40 - 45 °C
4: 1) KOtBu, 2) 10percent H2O2, 3N NaOH / 1) benzene; 24h, reflux; 24h, r.t.
5: 76 percent / 60percent HClO4 / 12 h / Ambient temperature
6: H2 / 10percent Pd/C / ethyl acetate / 48 h / 735.5 Torr / Ambient temperature
7: 81 percent / dioxane; pyridine / 14 h / 5 °C
8: 96 percent / 1-hydroxybenzotriazole, N,N'-dicyclohexylcarbodiimide / CH2Cl2 / 15 h / Ambient temperature
9: 96 percent / p-toluenesulfonic acid / benzene / 6 h / Heating
With
sodium hydroxide; perchloric acid; sulfuric acid; potassium tert-butylate; hydrogen; dihydrogen peroxide; nitric acid; benzotriazol-1-ol; toluene-4-sulfonic acid; dicyclohexyl-carbodiimide; sodium nitrite;
palladium on activated charcoal;
In
1,4-dioxane; pyridine; dichloromethane; water; acetic acid; ethyl acetate; benzene;
DOI:10.1002/jlac.198519850711