Hydrogen Peroxide → 4-Acetylbutyric acid

HRID 1759448Notes

Reaction equation

HRID 1759448 reaction equation
[O:1]=[O+][O-].C[C:5]1[CH2:10][CH2:9][CH2:8][C:7](=[O:11])[CH:6]=1.OO.[OH-:14].[Na+]>CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)C.[Cl-]>[O:14]=[C:5]([CH3:6])[CH2:10][CH2:9][CH2:8][C:7]([OH:11])=[O:1]

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 145113-Methyl-2-cyclohexen-1-oneHCID 14798Sodium HydroxideHCID 24823Ozone

Product 1

HCID 184074-Acetylbutyric acidYield 48%

Reagents, catalysts & solvents 1

HCID 21218Trioctylmethylammonium chlorideCatalyst

Conditions

Temperature
-20 °C

Procedure

Ozone was passed through a solution of 2.0 gms of 3-methyl-2-cyclohexenone at -78° C. for 30 minutes. The mixture was warmed to -20° C. and treated with a solution of 3.0 g of 30% hydrogen peroxide in 3.0 g of 50% NaOH. A drop of Adogen 464 was added and the two phase mixture was stirred vigorously for 1 hour. The aqueous phase was separated and acidified then extracted with ether. Removal of the ether afforded 1.12 g (48%) of 5-keto-hexanoic acid. The identity of the acid was confirmed by comparing the IR spectra of its methyl ester to the known spectra of the same compound.

Workup

  1. customThe aqueous phase was separated
  2. extractionacidified then extracted with ether
  3. customRemoval of the ether

Sources & evidence

ORD record
ord-d22c6be98e054e219ed23f0579aea1f4
Source dataset
uspto-grants-1982_07
Patent number
US04340753

Reaction notes

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