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Potassium Iodide → 6-(2-Propyl-3,4-dichlorophenoxy)hexanoic acid

HRID 34967
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 34967
[CH2:1]([C:4]1[C:9]([Cl:10])=[C:8]([Cl:11])[CH:7]=[CH:6][C:5]=1[OH:12])[CH2:2][CH3:3].Br[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]([OH:21])=[O:20].[H-].[Na+].[I-].[K+]>O.C(OCC)(=O)C.CN(C)P(N(C)C)(N(C)C)=O.O1CCCC1>[CH2:1]([C:4]1[C:9]([Cl:10])=[C:8]([Cl:11])[CH:7]=[CH:6][C:5]=1[O:12][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]([OH:21])=[O:20])[CH2:2][CH3:3]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

9

Edukt 4

HCID 4875Potassium IodideHCID 202106-Bromohexanoic acidHCID 24758Sodium hydrideHCID 6003603,4-Dichloro-2-propylphenol

Produkt 1

HCID 142330466-(2-Propyl-3,4-dichlorophenoxy)hexanoic acid

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 962Water
Lösungsmittel
HCID 8028TetrahydrofuranLösungsmittel
HCID 8857Ethyl AcetateLösungsmittel
HCID 12679HexamethylphosphoramideLösungsmittel

Versuchsvorschrift

To a solution of 1.1 g. of 2-propyl-3,4-dichlorophenol in 30 ml. of tetrahydrofuran and 30 ml. of hexamethylphosphoramide were added 4.1 g. of 6bromohexanoic acid. To the solution were then added 1.3 g. of a 50% oil dispersion of sodium hydride. A catalytic amount of potassium iodide was added and the reaction was stirred under a nitrogen atmosphere at 60°-70° C. overnight. The reaction was cooled to room temperature and ethyl acetate and water were added. The solution was evaporated to dryness. Fresh ethyl acetate and water were added and the layers were separated. Fresh ethyl acetate was added to the aqueous layer and the aqueous layer was adjusted to pH 2. The layers were separated and the organic layer was washed with a saturated sodium chloride solution. The organic layer was then filtered through sodium sulfate and evaporated to dryness. The resulting residue was extracted with hexane and evaporated to dryness to afford 500 mg. of the title compound.

Aufarbeitung

  1. additionTo the solution were then added 1.3 g
  2. customThe solution was evaporated to dryness
  3. additionFresh ethyl acetate and water were added
  4. customthe layers were separated
  5. additionFresh ethyl acetate was added to the aqueous layer
  6. customThe layers were separated
  7. washthe organic layer was washed with a saturated sodium chloride solution
  8. filtrationThe organic layer was then filtered through sodium sulfate
  9. customevaporated to dryness
  10. extractionThe resulting residue was extracted with hexane
  11. customevaporated to dryness
  12. customto afford 500 mg

Quellen und Nachweise

ORD-Eintrag
ord-e251a63eb2424cdea2c6965031dc78a9
Quelldatensatz
uspto-grants-1988_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04764521

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