sodium hydroxide T=0°C; 1 h;

1: With dimethylsulfide borane complex in tetrahydrofuran 12 h; Reflux; 2: With hydrogenchloride in tetrahydrofuran; methanol 2 h; Reflux; 3: With sodium hydroxide in tetrahydrofuran; methanol; water

1: SOCl2 / 3.5 h / 0 - 20 °C 2: 50 percent / triethylamine; K2CO3 / toluene / 2 h / Heating View Scheme

sodium hydroxide in 1,4-dioxane T=20°C; 12 h;

1: With sodium hydroxide in water T=170°C; P=5250.53 Torr; 3 h; Racemisation; 2: With hydrogenchloride in water T=20 - 25°C; pH=3.4;

1: With acetic anhydride; acetic acid T=100°C; 3 h; 2: With hydrogenchloride; water T=100°C; 5 h; 3: With sodium hydroxide in water T=0 - 5°C; pH=2.0 - 2.5; 1 h; Product distribution / selectivity;

in PtO2; acetic acid

1.1: sulfuric acid / 6 h / 80 °C 2.1: 31.4 g / CH2Cl2 / 20 °C 3.1: 72 percent / i-propylmagnesium chloride / tetrahydrofuran / 0.5 h / -10 °C 4.1: n-BuLi / tetrahydrofuran; hexane / 0.17 h / -78 °C 4.2: 56 percent / tetrahydrofuran; hexane / 0.25 h / -78 °C 5.1: 91 percent / iodine monochloride; 2,6-di-tert-butyl-4-methylpyridine / CH2Cl2 / 1 h / 20 °C 6.1: Mg / tetrahydrofuran / -78 °C 6.2: 77 percent / tetrahydrofuran / 1 h / -78 °C 7.1: 59 percent / formic acid / CH2Cl2 / 2 h / 20 °C 8.1: 45 percent / tri-n-butylphosphine; carbon tetrachloride / CH2Cl2 / 1 h / Heating 9.1: 80 percent Turnov. / K2CO3 / Pd(OAc)2 / H2O; methanol / 18 h / 20 °C / 760 Torr View Scheme