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

potassium hydroxide in 2-ethoxy-ethanol 3 h; Heating;

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

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