1: With sulfuric acid in methanol Cooling with ice; 2: With hydrogen; palladium on activated charcoal in methanol T=20°C; P=2585.81 Torr; 23 h; Inert atmosphere; 3: With sodium hydrogencarbonate; potassium carbonate in water pH=9 - 10; Reflux;

1: 96 percent / thionyl chloride / 1.) 0 deg C, 1 h, 2.) RT, overnight 2: 1.) LDA, N,N,N',N'-tetramethylenediamine / 1.) THF, hexanes, -75 deg C, 10 min, 2.) a.) -78 deg C, 1 h, b.) from -78 deg C to 0 deg C 3: H2 / Raney nickel / methanol; tetrahydrofuran / 46 h / 50 °C / 2585.7 Torr 4: toluene / 48 h / Heating View Scheme

1: 1.) LDA, N,N,N',N'-tetramethylenediamine / 1.) THF, hexanes, -75 deg C, 10 min, 2.) a.) -78 deg C, 1 h, b.) from -78 deg C to 0 deg C 2: H2 / Raney nickel / methanol; tetrahydrofuran / 46 h / 50 °C / 2585.7 Torr 3: toluene / 48 h / Heating View Scheme

in toluene 48 h; Heating; Yield given;

1: With lithium aluminium tetrahydride in tetrahydrofuran T=10°C; 21.85 h; Inert atmosphereReflux; 2: With water; sodium hydroxide in tetrahydrofuran Cooling with ice-water;