Hydrochloric Acid → HCID 56611240, compound

HRID 35486Notes

Reaction equation

HRID 35486 reaction equation
[CH2:1]([CH:9]1[C:13](=[CH:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20]([OH:22])=[O:21])[C:12](=O)[CH2:11][CH:10]1O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].Cl.[Cl-].[Na+].[O:28]1CCCC1>>[CH2:1]([CH:9]1[C:13](=[CH:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20]([OH:22])=[O:21])[CH2:12][C:11](=[O:28])[CH2:10]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 5234Sodium ChlorideHCID 8028TetrahydrofuranHCID 54546160HCID 54546160, compound

Product 1

HCID 56611240HCID 56611240, compoundYield 70%

Procedure

169 mg (0.5 mmole) of 4-octyl-5-(6-carboxyhexylidene)-3-hydroxycyclopentanone was dissolved in 3 ml of tetrahydrofuran, and ml of 0.5N hydrochloric acid was added. The mixture was stirred at room temperature for 4 days. A saturated aqueous solution of sodium chloride was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium chloride, and dried over anhydrous magnesium sulfate. The dried product was filtered, concentrated, and purified by preparative silica gel-thin-layer chromatography to give 12 mg (0.35 mmole; yield 70%) of 4-octyl-5-(6-carboxyhexylidene)-2-cyclopentanone. The resulting compound had the following spectral data.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with a saturated aqueous solution of sodium chloride
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationThe dried product was filtered
  5. concentrationconcentrated
  6. custompurified by preparative silica gel-thin-layer chromatography

Sources & evidence

ORD record
ord-866f8cfdf6db4b4a9f0b439c8c1829a2
Source dataset
uspto-grants-1988_08
Patent number
US04766147

Reaction notes

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