Water → 2-Methyl-6-oxoheptanoic acid

HRID 912407Notes

Reaction equation

HRID 912407 reaction equation
[Mn]([O-])(=O)(=O)=[O:2].[K+].[CH3:7][CH:8]1[CH2:13][CH2:12][CH2:11][CH:10]([CH3:14])[C:9]1=[O:15].[OH2:16]>>[CH3:7][CH:8]([CH2:13][CH2:12][CH2:11][C:10](=[O:2])[CH3:14])[C:9]([OH:15])=[O:16]

Participants

4

Reactant 3

HCID 962Water2×HCID 177802,6-DimethylcyclohexanoneHCID 516875Potassium Permanganate

Product 1

HCID 137172822-Methyl-6-oxoheptanoic acidYield 53.2%

Conditions

Temperature
30 °C

Procedure

A suspension of potassium permanganate (195.7 g, 1.24 mol) in water (1390 ml) was added carefully to a mixture of 2,6-dimethylcyclohexanone (120.0 g, 0.95 mol) and water (600 ml) while stirring vigorously the mixture at 30° C. or lower over a period of about 1 hour, and the mixture was stirred at room temperature overnight. The produced manganese dioxide was filtrated, and the filtration cake was washed with methyl tert-butyl ether (250 ml) and water (250 ml). The organic layer of the filtrate was separated, and the aqueous layer was adjusted to pH 1.0 with 35% concentrated hydrochloric acid (about 150 ml), and sodium chloride (400 g) was added and the mixture was extracted with ethyl acetate (300 ml×5), and the organic layer was dried over anhydrous magnesium sulfate, then, the solvent was distilled off under reduced pressure, and the resultant residual oil was distilled under reduced pressure by a vacuum pump. Fractions of boiling points of 130 to 144° C./267 Pa were collected, to obtain 79.92 g (yield 53.2%) of a racemate of 2-methyl-6-oxoheptanoic acid.

Workup

  1. stirringthe mixture was stirred at room temperature overnight
  2. filtrationThe produced manganese dioxide was filtrated
  3. washthe filtration cake was washed with methyl tert-butyl ether (250 ml) and water (250 ml)
  4. customThe organic layer of the filtrate was separated
  5. additionwas added
  6. extractionthe mixture was extracted with ethyl acetate (300 ml×5)
  7. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  8. distillationthe solvent was distilled off under reduced pressure
  9. distillationthe resultant residual oil was distilled under reduced pressure by a vacuum pump
  10. customFractions of boiling points of 130 to 144° C./267 Pa were collected

Sources & evidence

ORD record
ord-ac5a9a05d01245978e5d8c5522e64ab3
Source dataset
uspto-grants-2011_09
Patent number
US08026081B2

Reaction notes

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