1.1: hydrazine hydrate / ethane-1,2-diol / 1 h / Heating 1.2: 95 percent / potassium hydroxide / ethane-1,2-diol; H2O / 5 h / 195 - 197 °C 2.1: pyridine; ammonium chloride / 125 - 135 °C 2.2: acetic acid; chromium trioxide / H2O; 1,2-dichloro-ethane / 1 h / 20 °C 2.3: 57 percent / aluminium oxide / benzene / 2 h 3.1: 91.7 percent / hydrogen peroxide; sodium hydroxide / methanol / 2 h / 20 °C 4.1: 95 percent / pyridine / 20 °C 5.1: 70 percent / triethyl orthoformate; p-toluenesulfonic acid / CH2Cl2 / 20 h / 20 °C 6.1: 72 percent / tetrahydrofuran; diethyl ether / 72 h / 60 °C 7.1: m-iodoxybenzoic acid; diphenyl diselenide / toluene / 22 h / Heating 7.2: 50 percent / p-toluenesulfonic acid / CH2Cl2 / 4 h / 20 °C 8.1: perchloric acid; 1,3-dibromo-5,5-dimethylhydantoin / dimethylformamide / 3 h / cooling 8.2: 75.8 percent / sodium hydroxide / CH2Cl2; methanol; H2O / 2 h / cooling 9.1: 80 percent / hydrofluoric acid / tetrahydrofuran; CH2Cl2 / 5 h / -70 - 0 °C 10.1: 100 percent / anhydrous calcium chloride; calcium oxide; iodine / methanol / 1 h / 25 - 27 °C 11.1: 180 mg / acetic acid / acetone; H2O / 3 h / Heating 12.1: 90 percent / sodium methoxide; methanol / 4 h / 25 °C View Scheme

1: 100 percent / anhydrous calcium chloride; calcium oxide; iodine / methanol / 1 h / 25 - 27 °C 2: 180 mg / acetic acid / acetone; H2O / 3 h / Heating 3: 90 percent / sodium methoxide; methanol / 4 h / 25 °C View Scheme

1.1: 95 percent / pyridine / 20 °C 2.1: 72 percent / m-iodoxybenzoic acid; diphenyl diselenide / toluene / 12 h / Heating 3.1: hydrazine hydrate / ethane-1,2-diol / 1 h / Heating 3.2: 95 percent / potassium hydroxide / ethane-1,2-diol; H2O / 5 h / 195 - 197 °C 4.1: pyridine; ammonium chloride / 125 - 135 °C 4.2: acetic acid; chromium trioxide / H2O; 1,2-dichloro-ethane / 1 h / 20 °C 4.3: 57 percent / aluminium oxide / benzene / 2 h 5.1: 91.7 percent / hydrogen peroxide; sodium hydroxide / methanol / 2 h / 20 °C 6.1: 95 percent / pyridine / 20 °C 7.1: 70 percent / triethyl orthoformate; p-toluenesulfonic acid / CH2Cl2 / 20 h / 20 °C 8.1: 72 percent / tetrahydrofuran; diethyl ether / 72 h / 60 °C 9.1: m-iodoxybenzoic acid; diphenyl diselenide / toluene / 22 h / Heating 9.2: 50 percent / p-toluenesulfonic acid / CH2Cl2 / 4 h / 20 °C 10.1: perchloric acid; 1,3-dibromo-5,5-dimethylhydantoin / dimethylformamide / 3 h / cooling 10.2: 75.8 percent / sodium hydroxide / CH2Cl2; methanol; H2O / 2 h / cooling 11.1: 80 percent / hydrofluoric acid / tetrahydrofuran; CH2Cl2 / 5 h / -70 - 0 °C 12.1: 100 percent / anhydrous calcium chloride; calcium oxide; iodine / methanol / 1 h / 25 - 27 °C 13.1: 180 mg / acetic acid / acetone; H2O / 3 h / Heating 14.1: 90 percent / sodium methoxide; methanol / 4 h / 25 °C View Scheme

1.1: 72 percent / m-iodoxybenzoic acid; diphenyl diselenide / toluene / 12 h / Heating 2.1: hydrazine hydrate / ethane-1,2-diol / 1 h / Heating 2.2: 95 percent / potassium hydroxide / ethane-1,2-diol; H2O / 5 h / 195 - 197 °C 3.1: pyridine; ammonium chloride / 125 - 135 °C 3.2: acetic acid; chromium trioxide / H2O; 1,2-dichloro-ethane / 1 h / 20 °C 3.3: 57 percent / aluminium oxide / benzene / 2 h 4.1: 91.7 percent / hydrogen peroxide; sodium hydroxide / methanol / 2 h / 20 °C 5.1: 95 percent / pyridine / 20 °C 6.1: 70 percent / triethyl orthoformate; p-toluenesulfonic acid / CH2Cl2 / 20 h / 20 °C 7.1: 72 percent / tetrahydrofuran; diethyl ether / 72 h / 60 °C 8.1: m-iodoxybenzoic acid; diphenyl diselenide / toluene / 22 h / Heating 8.2: 50 percent / p-toluenesulfonic acid / CH2Cl2 / 4 h / 20 °C 9.1: perchloric acid; 1,3-dibromo-5,5-dimethylhydantoin / dimethylformamide / 3 h / cooling 9.2: 75.8 percent / sodium hydroxide / CH2Cl2; methanol; H2O / 2 h / cooling 10.1: 80 percent / hydrofluoric acid / tetrahydrofuran; CH2Cl2 / 5 h / -70 - 0 °C 11.1: 100 percent / anhydrous calcium chloride; calcium oxide; iodine / methanol / 1 h / 25 - 27 °C 12.1: 180 mg / acetic acid / acetone; H2O / 3 h / Heating 13.1: 90 percent / sodium methoxide; methanol / 4 h / 25 °C View Scheme

sulfuric acid in acetonitrile T=20°C; 20 h; Product distribution; Further Variations:Temperatures;

phosphate buffer; air; plasma of 20 d pregnant Sprague-Dawley rat T=37°C; 1 h; metabolism with tissues (plasma, liver, brain, placenta) from mothers and fetuses of Sprague-Dawley rats sacrificed on day 20 of pregnancy and mice on day 17 of pregnancy, further in vivo; Product distribution;

toluene-4-sulfonic acid in N,N-dimethyl-formamide; benzene 1.25 h; Ambient temperature;

1: 97 percent / periodic acid / methanol; H2O / 16 h / 20 °C 2: 1.) TEA, 2.) diisopropylamine / 1.) CH2Cl2, 0 deg C, 30 min, 2.) CH2Cl2, reflux, 1 h. 3: 1.) diphenyl chlorophosphate, TEA / 1.) THF, 55 deg C, 2 h, 2.) THF, DMF, 20 deg C, 2 h View Scheme