ammonium chloride; zinc in ethanol; water

water in acetonitrile T=25°C; pH 7.49; Rate constant;

nicotinium dichromate; toluene-4-sulfonic acid; acetic acid T=25.85°C; Kinetics; Further Variations:Temperatures;

1: K2CO3 / diethyl ether; H2O / 1 h / 0 °C 2: 66 percent / N-methylmorpholine / CH2Cl2 / 1) r.t to 40 deg C 2) 1 h 3: 100 percent / H2 / 10percent Pd-C / ethyl acetate / 760 Torr 4: 434 mg / DIBAL / tetrahydrofuran / 0.5 h / -78 °C View Scheme

1: K2CO3 / diethyl ether; H2O / 1 h / 0 °C 2: 66 percent / N-methylmorpholine / CH2Cl2 / 1) r.t to 40 deg C 2) 1 h View Scheme

1: K2CO3 / diethyl ether; H2O / 1 h / 0 °C 2: 66 percent / N-methylmorpholine / CH2Cl2 / 1) r.t to 40 deg C 2) 1 h 3: 100 percent / H2 / 10percent Pd-C / ethyl acetate / 760 Torr 4: 434 mg / DIBAL / tetrahydrofuran / 0.5 h / -78 °C 5: ethanol / 2 h / Heating 6: KOH / ethanol; H2O / 10 h / Heating View Scheme

1: K2CO3 / diethyl ether; H2O / 1 h / 0 °C 2: 66 percent / N-methylmorpholine / CH2Cl2 / 1) r.t to 40 deg C 2) 1 h 3: 100 percent / H2 / 10percent Pd-C / ethyl acetate / 760 Torr 4: 434 mg / DIBAL / tetrahydrofuran / 0.5 h / -78 °C 5: ethanol / 2 h / Heating View Scheme

1: K2CO3 / diethyl ether; H2O / 1 h / 0 °C 2: 66 percent / N-methylmorpholine / CH2Cl2 / 1) r.t to 40 deg C 2) 1 h 3: 100 percent / H2 / 10percent Pd-C / ethyl acetate / 760 Torr 4: 434 mg / DIBAL / tetrahydrofuran / 0.5 h / -78 °C 5: ethanol / 2 h / Heating 6: KOH / ethanol; H2O / 10 h / Heating 7: camphor-10-sulfonic acid / 12 h / Ambient temperature View Scheme

1: K2CO3 / diethyl ether; H2O / 1 h / 0 °C 2: 66 percent / N-methylmorpholine / CH2Cl2 / 1) r.t to 40 deg C 2) 1 h 3: 100 percent / H2 / 10percent Pd-C / ethyl acetate / 760 Torr View Scheme