Water → 3,3-Dimethyl-5-oxohexanoic acid

反応式

[O:1]=[C:2]1[CH2:9][C:6]([CH3:8])([CH3:7])[CH2:5][C:4](C)=[CH:3]1.[OH2:11].[O:12]=[O+][O-]>C(O)(=O)C>[O:11]=[C:4]([CH3:3])[CH2:5][C:6]([CH3:8])([CH3:7])[CH2:9][C:2]([OH:1])=[O:12]

参加物

反応条件

温度: 150 °C

実験手順

In accordance with the usual procedure 41 grams isophorone in 45 grams aqueous acetic acid (50% H2O) was ozonized at ambient temperature and pressure for approximately two hours. Additional acetic acid (60 mls) and water (30 mls) were added and treatment with ozone continued. After 8 hours no further ozone uptake was observed and the reaction was terminated. The resulting reaction product was then slowly added to refluxing acetic acid over a period of about one hour and, when a negative test was obtained using starch iodide, the water and acetic acid were stripped by gradually heating to 150° C. under a vacuum of 50-100 mm Hg. Distillation of the resulting crude product yielded 40.3 grams 5-keto-3,3-dimethylhexanoic acid (B.P. 96° C.-101° C. at 0.2 mm Hg) which was indicated by gas-liquid chromatography to be 99 percent pure.