1: 90 percent / sodium methoxide / methanol / 3 h / 0 °C 2: 97.5 percent / aq. KOH / 2-ethoxy-ethanol / 3 h / Heating 3: oxalyl chloride / CH2Cl2 / 3 h / Ambient temperature 4: AlCl3 / CS2 / 1.) 0 deg C, 1h, 2.) reflux, 30 min 5: 79 percent / NaBH4 / tetrahydrofuran; methanol / 0.5 h / Ambient temperature 6: 70 percent / p-toluenesulfonic acid / benzene / 0.5 h / Heating 7: 79 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / benzene / 0.17 h / Heating View Scheme

hydrogenchloride 1 h; Ambient temperature;

(i) PhLi, Et2O, (ii) /BRN= 1900390/, benzene, (iii) /BRN= 1098229/, HCl; Multistep reaction;

1: 90 percent / sodium methoxide / methanol / 3 h / 0 °C 2: 97.5 percent / aq. KOH / 2-ethoxy-ethanol / 3 h / Heating View Scheme

1: 90 percent / sodium methoxide / methanol / 3 h / 0 °C 2: 97.5 percent / aq. KOH / 2-ethoxy-ethanol / 3 h / Heating 3: oxalyl chloride / CH2Cl2 / 3 h / Ambient temperature 4: AlCl3 / CS2 / 1.) 0 deg C, 1h, 2.) reflux, 30 min 5: 79 percent / NaBH4 / tetrahydrofuran; methanol / 0.5 h / Ambient temperature 6: 70 percent / p-toluenesulfonic acid / benzene / 0.5 h / Heating View Scheme

1: 90 percent / sodium methoxide / methanol / 3 h / 0 °C 2: 97.5 percent / aq. KOH / 2-ethoxy-ethanol / 3 h / Heating 3: 80 percent / HCl / 0.33 h / 0 °C View Scheme