7-Octen-4-one, 2,6-dimethyl- → HCID 9964216, compound

HRID 1370029Notes

Reaction equation

HRID 1370029 reaction equation
[CH3:1][CH:2]([CH2:4][C:5]([CH2:7][CH:8](C=C)[CH3:9])=[O:6])[CH3:3].[C:12](=[O:15])(O)[O-:13].[Na+].I([O-])(=O)(=O)=O.[Na+].[Mn]([O-])(=O)(=O)=O.[K+].S(=O)(O)[O-].[Na+]>CC(C)=O.O.C1COCC1.O>[CH3:9][CH:8]([CH2:7][C:5](=[O:6])[CH2:4][CH:2]([CH3:3])[CH3:1])[C:12]([OH:13])=[O:15]

Participants

8

Reactant 5

HCID 1027067-Octen-4-one, 2,6-dimethyl-HCID 516875Potassium PermanganateHCID 516892Sodium BicarbonateHCID 23665763Sodium BisulfiteHCID 23667635Sodium periodate

Product 1

HCID 9964216HCID 9964216, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 18366337Propan-2-one--water (1/1)SolventHCID 21881883Oxolane--water (1/1)Solvent

Conditions

Temperature
4 °C

Procedure

A mixture of dihydrotagetone (4) (3.53 g, 22.92 mmole), sodium bicarbonate (1.8 g, 21.43 mmole), sodium metaperiodate (22.84 g, 106.78 mmole), potassium permanganate (0.65 g, 4.11 mmole), alumina (0.8-1.2 g) and THF-water or acetone-water (20 mL, 1:3) was taken in a 250 ml Erlenmeyer flask fitted with a loose funnel at the top. The flask was shaken well for a while and then placed inside a microwave oven (Kenstar) operating at medium power (600 W) and irradiated for 2-20 minutes in parts. After completion of the reaction (monitored by TLC), the contents of the flask were poured into saturated solution of sodium bisulphite to destroy excess permanganate and resulting mixture was passed through a bed of Celite and further washed with aqueous acetone (40 mL×3, 3:1). The filtrate and washings were combined and the solution concentrated under reduced pressure to remove acetone. The mixture was cooled to 0 to 8° C. and acidified with dilute acid and then extracted with ethylacetate (3×25 mL). The ethylacetate layers were then combined, washed with saturated sodium bisulphite and sodium chloride (3×15 mL), dried over anhydrous sodium sulphate and then filtered. The solvent was removed to afford a crude product which was purified on silica column as above which afforded 2,6-dimethyl-4-oxo-heptanoic acid (3) in 81% yield as a viscous liquid. The physical and spectral data was found similar as above (Example II-i).

Workup

  1. customfitted with a loose funnel at the top
  2. customplaced inside a microwave oven
  3. customirradiated for 2-20 minutes in parts
  4. customAfter completion of the reaction (monitored by TLC)
  5. customto destroy excess permanganate
  6. customresulting mixture
  7. washfurther washed with aqueous acetone (40 mL×3, 3:1)
  8. concentrationthe solution concentrated under reduced pressure
  9. customto remove acetone
  10. additionwith dilute acid
  11. extractionextracted with ethylacetate (3×25 mL)
  12. washwashed with saturated sodium bisulphite and sodium chloride (3×15 mL)
  13. dry with materialdried over anhydrous sodium sulphate
  14. filtrationfiltered
  15. customThe solvent was removed
  16. customto afford a crude product which
  17. customwas purified on silica column as above which

Sources & evidence

ORD record
ord-619794d40dc147a1ad139251af66e3bf
Source dataset
uspto-grants-2003_06
Patent number
US06579992B2

Reaction notes

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