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Eicosanoic Acid → Eicosanoyl chloride

HRID 514286
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 514286
[C:1](Cl)(=O)[C:2]([Cl:4])=[O:3].[C:7](O)(=O)[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]CC>CN(C=O)C.ClCCl>[C:2]([Cl:4])(=[O:3])[CH2:1][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH3:7]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 2

HCID 10467Eicosanoic AcidHCID 65578Oxalyl chloride

Produkt 1

HCID 9862365Eicosanoyl chlorideAusbeute 100,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideKatalysatorHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Oxalyl chloride (2.67 ml, 0.0191 mol) was added drop-wise to a mixture of Arachidic acid (6.0 g, 0.0211 mol) and DMF (4 drops) in dichloromethane (50 ml) at 0° C. After the addition was completed, the reaction mixture was stirred at 0° C. for 30 minutes and then stirred at 25° C. for 1 hour, the reaction mixture was partitioned between dichloromethane and water, and the aqueous layer was extracted with dichloromethane. The combined organic extracts were washed with brine, then dried with sodium sulphate and concentrated in vacuo to provide the desired product (6.35 g, 100% yield) as a solid which was not purified any further.

Aufarbeitung

  1. additionAfter the addition
  2. stirringstirred at 25° C. for 1 hour
  3. customthe reaction mixture was partitioned between dichloromethane and water
  4. extractionthe aqueous layer was extracted with dichloromethane
  5. washThe combined organic extracts were washed with brine
  6. dry with materialdried with sodium sulphate
  7. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-f5f6671ad908457abd09f8683567ffdf
Quelldatensatz
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09107911B2

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