Acetic Acid → 3,3-Dimethyl-5-oxohexanoic acid
Reaction equation
[O:1]=[C:2]1[CH2:9]C(C)(C)[CH2:5][C:4]([CH3:10])=[CH:3]1.[C:11]([OH:14])(=[O:13])[CH3:12]>>[O:1]=[C:2]([CH3:9])[CH2:3][C:4]([CH3:10])([CH3:5])[CH2:12][C:11]([OH:14])=[O:13]Participants
3
Procedure
In a manner similar to that described in Example I, 30 grams isophorone in 57 grams aqueous acetic acid (35% H2O) was ozonized at ambient temperature and pressure in a 300 ml glass cylinder for approximately 5 1/2 hours. The resulting reaction product was then slowly dropped into a small amount of refluxing acetic acid, stripped at 140° C. under vacuum to remove water and acetic acid, and then vacuum distilled. Ninety-five percent yield of high purity 5-keto-3,3-dimethylhexanoic acid was obtained boiling in the range 96° C.-106° C. (0.1 mm Hg).
Workup
- customwas ozonized at ambient temperature
- customfor approximately 5 1/2 hours
- customThe resulting reaction product
- customstripped at 140° C. under vacuum
- customto remove water and acetic acid
- distillationvacuum distilled
Sources & evidence
- ORD record
- ord-20f90135b5c2457a938306c1e8b9ae9c
- Source dataset
- uspto-grants-1986_12
- Patent number
- US04628117
Reaction notes
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