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

Participants

Reaction Conditions

Reaction Steps

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.

Provenance & Evidence