1: thionyl chloride / benzene / 2 h / Heating 2: aq. NaOH / benzene / 1 h 3: 76 percent / POCl3 / 1 h / 100 °C 4: NaBH4, AcOH / CH2Cl2 / 4 h / 0 - 5 °C 5: 81 percent / HCOOH / 0.25 h / 100 °C View Scheme

hydrogenchloride; tin(ll) chloride in acetic acid 6.75 h; Heating;

1: 66 percent / aq NaHSO3 / H2O / 100 °C / 1.) -5 deg C, 105 min 2.) 0 deg C, 33 min, 5N H2SO4 2: 51 percent / SnCl2*2H2O, HCl / acetic acid / 6.75 h / Heating View Scheme

hydrogenchloride; sulfuric acid 1) H2O, 0-5 deg C, 5 h, 2) H2O, reflux, 2 h; Yield given. Multistep reaction;

1: aq. 5percent NaOH / 1.5 h / Heating 2: NaBH4, aq. 5percent NaOH / 6 h / Heating 3: aq. 12 N HCl / 3 h / Heating View Scheme

1: 1) s-BuLi, N,N,N,N-tetramethylethylene diamine / 1) THF, cyclohexane, -78 deg C, 1 h, 2) to room temperature, 12 h 2: aq. 5percent NaOH / 1.5 h / Heating 3: NaBH4, aq. 5percent NaOH / 6 h / Heating 4: aq. 12 N HCl / 3 h / Heating View Scheme