1: 82 percent / fumaric acid / benzene / 68 h / Heating; azeotropic removal of water 2: DIBAL / toluene / 7 h / -78 °C 3: oxalic acid / CH2Cl2; H2O / 3.5 h / Ambient temperature 4: 78 percent / imidazole / dimethylformamide / 65 h / Ambient temperature 5: 1.) OsO4, 2.) aq. NaHSO3 / 1.) a) pyridine, 0-5 deg C, b) RT, 5 h, 2.) pyridine, RT, 3 h 6: 94 percent / pyridine / 10 h / 4 °C 7: 67 percent / SeO2 / 2-methyl-propan-2-ol; benzene / Heating 8: 88 percent / acetic acid (glacial) / tetrahydrofuran; H2O / 162 h / Ambient temperature View Scheme

potassium hydroxide; 3-chloro-benzenecarboperoxoic acid in dichloromethane T=20°C; 0.833333 h;