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Hydrochloric Acid → (+/-)-Cyclopentyl[4-(trifluoromethyl)phenyl]acetic acid

HRID 1475647
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1475647
[CH:1]1([CH:6]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=2)[C:7]([O:9]C)=[O:8])[CH2:5][CH2:4][CH2:3][CH2:2]1.C1COCC1.[OH-].[Li+].Cl>O.CO>[CH:1]1([CH:6]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:18])([F:19])[F:20])=[CH:13][CH:12]=2)[C:7]([OH:9])=[O:8])[CH2:5][CH2:4][CH2:3][CH2:2]1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 68006808Methyl cyclopentyl[4-(trifluoromethyl)phenyl]acetate

Produkt 1

HCID 67078122(+/-)-Cyclopentyl[4-(trifluoromethyl)phenyl]acetic acidAusbeute 96,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887
Methanol
Lösungsmittel
HCID 962WaterLösungsmittel2×

Versuchsvorschrift

4.98 g (17.4 mmol) of methyl cyclopentyl[4-(trifluoromethyl)phenyl]acetate were initially charged in a mixture of in each case 24.9 ml of THF, methanol and water, and 1.04 g (43.49 mmol) of lithium hydroxide were added at 0° C. The reaction mixture was warmed to RT and stirred at this temperature for 4 h. The mixture was then diluted with water and acidified slightly with 1 N hydrochloric acid. The aqueous phase was extracted three times with ethyl acetate. The combined organic phases were dried over magnesium sulphate and concentrated under reduced pressure. This gave 4.56 g of the target compound as a crude product (yield 96.3% of theory).

Aufarbeitung

  1. additionwere added at 0° C
  2. extractionThe aqueous phase was extracted three times with ethyl acetate
  3. dry with materialThe combined organic phases were dried over magnesium sulphate
  4. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-9751a17c1af34d9aac3f9dc0fda7ff81
Quelldatensatz
uspto-grants-2015_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09018258B2

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