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Ethyl 3-(trifluoromethyl)non-2-enoate → HCID 54107361, Verbindung

HRID 2073423
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2073423
[F:1][C:2]([F:17])([F:16])[C:3]([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])=[CH:4][C:5]([O:7]CC)=[O:6].[H][H]>CO.[Pd]>[F:1][C:2]([F:16])([F:17])[C:3]([CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])=[CH:4][C:5]([OH:7])=[O:6]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 2

HCID 53647231Ethyl 3-(trifluoromethyl)non-2-enoateHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 54107361HCID 54107361, VerbindungAusbeute 112,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

13.78 g of ethyl 3-trifluoromethyl-2-nonenoate was dissolved in 138 ml of methanol, and 1.38 g of 5%-palladium/activated carbon was added thereto, followed by stirring for 4 hours at room temperature and normal pressure in a hydrogen atmosphere in a catalytic hydrogenation apparatus. After the reaction, the 5%-palladium/activated carbon was filtered out, and the remaining methanol solution was mixed with 24 ml, of water and 20 g of potassium hydroxide, followed by 2 hours of heat refluxing, distilling-off of methanol under a reduced pressure, acidification with addition of 6N-hydrochloric acid, and extraction with methylene chloride. The resultant methylene chloride solution was dried on sodium sulfate, followed by distilling-off of the solvent and purification by distillation (b.p.: 118.5-119.7° C./20 mmHg), whereby 13.78 g of 3-trifluoromethylnonenoic acid was obtained. (Yield: 51.5%).

Aufarbeitung

  1. customAfter the reaction
  2. filtrationthe 5%-palladium/activated carbon was filtered out
  3. additionthe remaining methanol solution was mixed with 24 ml, of water and 20 g of potassium hydroxide
  4. waitfollowed by 2 hours
  5. temperatureof heat
  6. temperaturerefluxing, distilling-off of methanol under a reduced pressure, acidification with addition of 6N-hydrochloric acid, and extraction with methylene chloride
  7. dry with materialThe resultant methylene chloride solution was dried on sodium sulfate
  8. distillationfollowed by distilling-off of the solvent and purification by distillation (b.p.: 118.5-119.7° C./20 mmHg)

Quellen und Nachweise

ORD-Eintrag
ord-c0211d1413ea4ed4a582f37ae66da782
Quelldatensatz
uspto-grants-1990_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04917817

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