potassium carbonate in N,N-dimethyl-formamide T=60°C; 12 h; Inert atmosphere;

potassium carbonate in N,N-dimethyl-formamide T=100°C; 20 h;

1: 65.6 percent / LiAlH4 / tetrahydrofuran / 1.5 h / Ambient temperature 2: 88.8 percent / SOCl2 / benzene; CH2Cl2; pyridine / below 10 deg C, then 4 deg C, 1 h View Scheme

sodium hydroxide in 1,4-dioxane; methanol; water 14 h; Reflux;

1: aq. NaOH / ethanol / Heating 2: 80 percent / LiAlH4 / tetrahydrofuran / Heating 3: 90 percent / thionyl chloride, pyridine / diethyl ether 4: 65 percent / Heating 5: 75 percent / aq. NaOH / ethanol / Heating View Scheme

1: 1.99 g / NaOH / methanol; H2O / 3 h / Heating 2: oxalyl chloride; DMF / hexane; CH2Cl2 / 0.5 h / 0 °C View Scheme