1: dicyclocarbodiimide; 4-dimethylaminopyridine / CH2Cl2 / 25 °C 2: 45.3 g / aq. H2O2 / phenol / 25 °C 3: 90 percent / Zn; aq. NH4OAc / tetrahydrofuran / 6 - 8 °C 4: 94 percent / toluene / 2 h / Heating 5: I2 / CH2Cl2 / 25 °C 6: 7.24 g / aq. KMnO4 / acetic acid / 0.33 h / ultrasounds 7: 90 percent / m-cresol / 3 h / 50 °C View Scheme

1.1: H2SO4; KBr / ethanol / 0 - 5 °C 1.2: 91 percent / aq. NaNO2 / ethanol / 0 - 5 °C 2.1: dicyclocarbodiimide; 4-dimethylaminopyridine / CH2Cl2 / 25 °C 3.1: 45.3 g / aq. H2O2 / phenol / 25 °C 4.1: 90 percent / Zn; aq. NH4OAc / tetrahydrofuran / 6 - 8 °C 5.1: 94 percent / toluene / 2 h / Heating 6.1: I2 / CH2Cl2 / 25 °C 7.1: 7.24 g / aq. KMnO4 / acetic acid / 0.33 h / ultrasounds 8.1: 90 percent / m-cresol / 3 h / 50 °C View Scheme

1: 7.24 g / aq. KMnO4 / acetic acid / 0.33 h / ultrasounds 2: 90 percent / m-cresol / 3 h / 50 °C View Scheme

1: I2 / CH2Cl2 / 25 °C 2: 7.24 g / aq. KMnO4 / acetic acid / 0.33 h / ultrasounds 3: 90 percent / m-cresol / 3 h / 50 °C View Scheme

1: 45.3 g / aq. H2O2 / phenol / 25 °C 2: 90 percent / Zn; aq. NH4OAc / tetrahydrofuran / 6 - 8 °C 3: 94 percent / toluene / 2 h / Heating 4: I2 / CH2Cl2 / 25 °C 5: 7.24 g / aq. KMnO4 / acetic acid / 0.33 h / ultrasounds 6: 90 percent / m-cresol / 3 h / 50 °C View Scheme

1: 94 percent / toluene / 2 h / Heating 2: I2 / CH2Cl2 / 25 °C 3: 7.24 g / aq. KMnO4 / acetic acid / 0.33 h / ultrasounds 4: 90 percent / m-cresol / 3 h / 50 °C View Scheme

1: 90 percent / Zn; aq. NH4OAc / tetrahydrofuran / 6 - 8 °C 2: 94 percent / toluene / 2 h / Heating 3: I2 / CH2Cl2 / 25 °C 4: 7.24 g / aq. KMnO4 / acetic acid / 0.33 h / ultrasounds 5: 90 percent / m-cresol / 3 h / 50 °C View Scheme

sodium 2-ethyl hexanoate in methanol; water; isopropyl alcohol T=0 - 35°C; 2.5 - 3.25 h; Product distribution / selectivity;

sodium 2-ethyl hexanoate in methanol; water; isopropyl alcohol T=0 - 35°C; 2.5 - 3.25 h; Product distribution / selectivity;