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

HRID 851801

Reaction equation

HRID 851801 reaction equation
I([O-])(=O)(=O)=O.Cl[O-].[Na+].[O:9]=[C:10]1[CH2:17][C:14]([CH3:16])([CH3:15])[CH2:13]C(C)=[CH:11]1.[C:19](=[O:22])([O-])[O-:20].[Na+].[Na+]>C(Cl)Cl>[O:9]=[C:10]([CH3:11])[CH2:17][C:14]([CH3:16])([CH3:15])[CH2:13][C:19]([OH:20])=[O:22]

Participants

6

Reactant 4

HCID 6544Isophorone2×HCID 10340Sodium CarbonateHCID 167232PeriodateHCID 23665760Sodium Hypochlorite2×

Product 1

HCID 113326103,3-Dimethyl-5-oxohexanoic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

The above oxidation procedure was repeated, except that in place of periodate there was utilized sodium hypochlorite. There was added slowly about 2700 parts of an aqueous 5% sodium hypochlorite solution to a solution of 56 parts of isophorone in about 200 parts of methylene chloride. An exothermic reaction resulted causing the methylene chloride to reflux. The organic phase was analyzed shortly after the addition was complete and it was found that all of the isophorone had reacted. The aqueous layer was made basic with sodium carbonate and the reaction mixture was filtered. The aqueous phase was washed with methylene chloride and then acidified by slowly adding it to a 2 phase mixture of concentrated hydrochloric acid and methylene chloride. The organic phase was separated and the aqueous phase was extracted with several portions of fresh methylene chloride. Upon combining the various organic layers which were dried and evaporated, there was obtained 37.7 parts of 5-keto-3,3-dimethylhexanoic acid.

Workup

  1. customAn exothermic reaction
  2. customresulted
  3. temperatureto reflux
  4. additionafter the addition
  5. customhad reacted
  6. filtrationthe reaction mixture was filtered
  7. washThe aqueous phase was washed with methylene chloride
  8. additionby slowly adding it
  9. additionto a 2 phase mixture of concentrated hydrochloric acid and methylene chloride
  10. customThe organic phase was separated
  11. extractionthe aqueous phase was extracted with several portions of fresh methylene chloride
  12. customwere dried
  13. customevaporated

Sources & evidence

ORD record
ord-02e1602c1027497591c7e61a162c4136
Source dataset
uspto-grants-1983_05
Patent number
US04386222

Linked notes

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