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Gamma-undecalactone → 4-Hydroxy-undecanoic acid dodecylamide

HRID 1169179
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1169179
[Cl-].[Al+3].[Cl-].[Cl-].[CH2:5]([NH2:17])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].[CH3:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH:25]1[O:30][C:28](=[O:29])[CH2:27][CH2:26]1>C(Cl)Cl>[CH2:5]([NH:17][C:28](=[O:29])[CH2:27][CH2:26][CH:25]([OH:30])[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH3:18])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 7714Gamma-undecalactoneHCID 13583DodecylamineHCID 6451240Aluminum(III) Chloride

Produkt 1

HCID 539853184-Hydroxy-undecanoic acid dodecylamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A solution of 19.0 g aluminum chloride, dissolved in methylene chloride, was cooled to 0° C. and 46.5 g dodecylamine in methylene chloride was added dropwise (exothermic). At room temperature, 19.3 g gamma-undecalactone was added rapidly. The temperature rose to 36° C. The reaction was stirred at room temperature for 4 hours. The mixture was quenched with water and filtered over Celite. The liquid was extracted with ether and washed with water and brine. The solution was dried, filtered and evaporated to dryness. The resulting brown crystals were purified by recrystallization from ether/ethylacetate to give pale yellow crystals.

Aufarbeitung

  1. customrose to 36° C
  2. customThe mixture was quenched with water
  3. filtrationfiltered over Celite
  4. extractionThe liquid was extracted with ether
  5. washwashed with water and brine
  6. customThe solution was dried
  7. filtrationfiltered
  8. customevaporated to dryness
  9. customThe resulting brown crystals were purified by recrystallization from ether/ethylacetate
  10. customto give pale yellow crystals

Quellen und Nachweise

ORD-Eintrag
ord-6c125135a4af4638aa453a49284d6ecb
Quelldatensatz
uspto-grants-2003_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06627763B2

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