Acetic Acid → 3,3-Dimethyl-5-oxohexanoic acid

HRID 1248999Notes

Reaction equation

HRID 1248999 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=[O+][O-]>O>[O:1]=[C:2]([CH3:9])[CH2:3][C:4]([CH3:10])([CH3:5])[CH2:12][C:11]([OH:14])=[O:13]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 6544Isophorone2×HCID 24823Ozone

Product 1

HCID 113326103,3-Dimethyl-5-oxohexanoic acidYield 87%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Isophorone was ozonized in the presence of 0.23% manganous acetate. For the reaction 43 grams isophorone, 120 grams acetic acid, 60 grams water and 100 milligrams Mn(OAc)2. 4H2O were charged to the reactor and ozonized in the usual manner at ambient temperature and pressure. The essentially colorless reaction mixture developed a slight greenish coloration after about three hours and after six hours was dark brown. Ozone addition was terminated at this point. The absence of active oxygen made any decomposition precautionary step unnecessary and the reaction mixture was directly treated under vacuum to strip off acetic acid and water. Vacuum distillation of the resulting crude product at 0.3 mm Hg gave an 87 percent yield of 96.5% pure 5-keto-3,3-dimethylhexanoic acid boiling in the range 95° C. to 100° C.

Workup

  1. addition4H2O were charged to the reactor
  2. customozonized in the usual manner at ambient temperature
  3. customafter about three hours
  4. customwas terminated at this point
  5. additionwas directly treated under vacuum
  6. distillationVacuum distillation of the resulting crude product at 0.3 mm Hg

Sources & evidence

ORD record
ord-2cac17670cbb4bab9b67ee2c2116b23a
Source dataset
uspto-grants-1986_12
Patent number
US04628117

Reaction notes

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