potassium hydroxide; air in tetrahydrofuran; water 1 h;

1: With sodium ethanolate in ethanol Claisen condensation; 0.333333 h; Heating; 2: With air in ethanol T=20°C; 48 h;

1: OsO4; N-methylmorpholine N-oxide; pyridine / tetrahydrofuran; 2-methyl-propan-2-ol; H2O / 12 h 2: 91 mg / 1-hydroxy-1,2-benziodoxol-3(1H)-one 1-oxide / dimethylsulfoxide; tetrahydrofuran / 0.5 h 3: 132 mg / aq. KOH; air / tetrahydrofuran / 10 - 20 °C View Scheme

1: AcOH / 2 h / 40 °C / Irradiation 2: 72 percent / aq. HCl / acetic acid / 4 h / 90 °C 3: OsO4; N-methylmorpholine N-oxide; pyridine / tetrahydrofuran; 2-methyl-propan-2-ol; H2O / 12 h 4: 91 mg / 1-hydroxy-1,2-benziodoxol-3(1H)-one 1-oxide / dimethylsulfoxide; tetrahydrofuran / 0.5 h 5: 132 mg / aq. KOH; air / tetrahydrofuran / 10 - 20 °C View Scheme

1: 91 mg / 1-hydroxy-1,2-benziodoxol-3(1H)-one 1-oxide / dimethylsulfoxide; tetrahydrofuran / 0.5 h 2: 132 mg / aq. KOH; air / tetrahydrofuran / 10 - 20 °C View Scheme

1: 72 percent / aq. HCl / acetic acid / 4 h / 90 °C 2: OsO4; N-methylmorpholine N-oxide; pyridine / tetrahydrofuran; 2-methyl-propan-2-ol; H2O / 12 h 3: 91 mg / 1-hydroxy-1,2-benziodoxol-3(1H)-one 1-oxide / dimethylsulfoxide; tetrahydrofuran / 0.5 h 4: 132 mg / aq. KOH; air / tetrahydrofuran / 10 - 20 °C View Scheme

1: With N-methylamine hydrochloride; toluene-4-sulfonic acid in benzene T=80°C; Mannich reaction; 1 h; 2: With palladium on activated charcoal; hydrogen in ethyl acetate T=20°C; 18 h;

1: 82 percent / toluene / 2 h / UV-irradiation 2: 86 percent / CrO3*2Py / CH2Cl2 / 1 h / 0 - 25 °C 3: 71 percent / acetic acid / 2 h / UV-irradiation 4: 72 percent / HCl; acetic acid / H2O / 0.5 h / 70 °C 5: 92 percent / OsO4; N-methylmorpholine N-oxide; pyridine / tetrahydrofuran; 2-methyl-propan-2-ol; H2O / 12 h 6: 92 percent / 1-hydroxy-1,2-benzodioxol-3(1H)-one 1-oxide / dimethylsulfoxide / 1 h / 20 °C 7: 87 percent / potassium hydroxide; air / H2O; tetrahydrofuran / 1 h View Scheme

1: With argentic oxide; nitric acid in 1,4-dioxane; water T=20°C; 0.0333333 h; 2: With sodium hydroxide in methanol; water T=20°C; 0.5 h; Title compound not separated from byproducts;

argentic oxide; nitric acid in 1,4-dioxane; water T=20°C; 0.0333333 h;