Hydrochloric Acid → HCID 56614735, compound

HRID 1789620Notes

Reaction equation

HRID 1789620 reaction equation
OO.[CH3:3][O:4][C:5]([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH:13]1[C:17](=[CH:18][CH:19]=[CH:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[C:16](=[O:26])[CH:15]=[CH:14]1)=[O:6].[OH-].[Na+].[Cl-:29].[NH4+].Cl>CO.CC(C)=O>[Cl:29][C:15]1[C:16](=[O:26])[C:17](=[CH:18][CH:19]=[CH:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[CH:13]([CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][C:5]([O:4][CH3:3])=[O:6])[CH:14]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 25517Ammonium ChlorideHCID 56614389HCID 56614389, compound

Product 1

HCID 56614735HCID 56614735, compoundYield 55%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 887MethanolSolvent

Procedure

0.5 ml of 30% aqueous hydrogen peroxide was added to a solution of 95 mg (286 mmol) of 4-(6-methoxycarbonylhexyl)-5-(2-octenylidene)-2-cyclopentenone in 4 ml of methanol under ice cooling and stirring, and then 0.1 ml of 1N sodium hydroxide was added. The mixture was stirred at 0° C. for 20 minutes. A saturated aqueous solution of ammonium chloride was added, and the mixture was extracted with hexane. The organic layer was washed with a saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulfate. The dried product was filtered and concentrated to give an oily product. The product was dissolved in 3 ml of acetone, and 0.5 ml of concentrated hydrochloric acid was added, the mixture was extracted with ethylacetate. The organic layer was washed with a saturated aqueous solution of sodium chloride and dried over an anhydrous sodium sulfate. The product was filtered, concentrated and subjected to silica gel column chromatography (silica gel, 10 g; eluent, cyclohexane:ethylacetate=10:1) to give 58 mg (yield 55%) of 2-chloro-4-(6-methoxycarbonylhexyl)-5-(2-octenylidene)-2-cyclopentenone.

Workup

  1. stirringThe mixture was stirred at 0° C. for 20 minutes
  2. extractionthe mixture was extracted with hexane
  3. washThe organic layer was washed with a saturated aqueous solution of sodium chloride
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationThe dried product was filtered
  6. concentrationconcentrated
  7. customto give an oily product
  8. extractionthe mixture was extracted with ethylacetate
  9. washThe organic layer was washed with a saturated aqueous solution of sodium chloride
  10. dry with materialdried over an anhydrous sodium sulfate
  11. filtrationThe product was filtered
  12. concentrationconcentrated

Sources & evidence

ORD record
ord-71e1a1b0be144d6eb80b570d1d6aa41b
Source dataset
uspto-grants-1987_08
Patent number
US04689426

Reaction notes

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