sulfuric acid 5 h; Heating;

hydroxide; hydrazine in diethylene glycol T=210°C;

sodium dithionite; sodium hydrogencarbonate in water; N,N-dimethyl-formamide Heating;

sulfuric acid 24 h; Heating;

1: 75 percent / aq. NaOH / tetrabutylammonium bromide / CH2Cl2 / 1 h / Ambient temperature 2: 58 percent / NaOMe / benzene; methanol / 0.5 h / Heating 3: 60 percent / Na2S2O4, NaHCO3 / dimethylformamide; H2O / Heating View Scheme

1: 90.5 percent / Br2 / Fe / I2 / CCl4 2: 91.6 percent / N-bromsuccinimide, dibenzoylperoxide / CCl4 / 6 h / Heating 3: 1.)NaOEt / 1.)EtOH, reflux, 2 h, 2.)reflux, 16 h 4: 58.7 percent / 5N NaOH / methanol / 2.25 h / Heating 5: 68 percent / 6N HCl / 16 h / Heating 6: thionyl chloride / CH2Cl2 / 4 h / Heating 7: anh. AlCl3 / CH2Cl2 / 2 h / Heating 8: 55.4 percent / LiAlH4 / tetrahydrofuran / 192 h / Heating 9: 85 percent / 10percent H2SO4 / 24 h / Heating View Scheme

1: 1.)NaOEt / 1.)EtOH, reflux, 2 h, 2.)reflux, 16 h 2: 58.7 percent / 5N NaOH / methanol / 2.25 h / Heating 3: 68 percent / 6N HCl / 16 h / Heating 4: thionyl chloride / CH2Cl2 / 4 h / Heating 5: anh. AlCl3 / CH2Cl2 / 2 h / Heating 6: 55.4 percent / LiAlH4 / tetrahydrofuran / 192 h / Heating 7: 85 percent / 10percent H2SO4 / 24 h / Heating View Scheme

1: 91.6 percent / N-bromsuccinimide, dibenzoylperoxide / CCl4 / 6 h / Heating 2: 1.)NaOEt / 1.)EtOH, reflux, 2 h, 2.)reflux, 16 h 3: 58.7 percent / 5N NaOH / methanol / 2.25 h / Heating 4: 68 percent / 6N HCl / 16 h / Heating 5: thionyl chloride / CH2Cl2 / 4 h / Heating 6: anh. AlCl3 / CH2Cl2 / 2 h / Heating 7: 55.4 percent / LiAlH4 / tetrahydrofuran / 192 h / Heating 8: 85 percent / 10percent H2SO4 / 24 h / Heating View Scheme

1: 55.4 percent / LiAlH4 / tetrahydrofuran / 192 h / Heating 2: 85 percent / 10percent H2SO4 / 24 h / Heating View Scheme

1: anh. AlCl3 / CH2Cl2 / 2 h / Heating 2: 55.4 percent / LiAlH4 / tetrahydrofuran / 192 h / Heating 3: 85 percent / 10percent H2SO4 / 24 h / Heating View Scheme