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

HRID 1248998

Reaction equation

HRID 1248998 reaction equation
[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]

Participants

5

Reactant 3

HCID 962Water2×HCID 6544IsophoroneHCID 24823Ozone2×

Product 1

HCID 113326103,3-Dimethyl-5-oxohexanoic acid

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent4×

Conditions

Temperature
150 °C

Procedure

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.

Workup

  1. customwas ozonized at ambient temperature
  2. customthe reaction was terminated
  3. customThe resulting reaction product
  4. additionwas then slowly added
  5. customwhen a negative test was obtained
  6. distillationDistillation of the resulting crude product

Sources & evidence

ORD record
ord-f8c4c72976c243f59536e23d029e0efc
Source dataset
uspto-grants-1986_12
Patent number
US04628117

Linked notes

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