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2-Propenoic acid, 3-[4-(trifluoromethyl)phenyl]-, ethyl ester → (E)-3-(4-(trifluoromethyl)phenyl)prop-2-en-1-ol

HRID 381428
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 381428
[F:1][C:2]([F:17])([F:16])[C:3]1[CH:15]=[CH:14][C:6](/[CH:7]=[CH:8]/[C:9](OCC)=[O:10])=[CH:5][CH:4]=1.[H-].C([Al+]CC(C)C)C(C)C.C1(C)C=CC=CC=1>C1(C)C=CC=CC=1>[F:1][C:2]([F:16])([F:17])[C:3]1[CH:15]=[CH:14][C:6](/[CH:7]=[CH:8]/[CH2:9][OH:10])=[CH:5][CH:4]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 115070152-Propenoic acid, 3-[4-(trifluoromethyl)phenyl]-, ethyl esterHCID 86583787Diisobutylaluminumhydride toluene

Produkt 1

HCID 10512285(E)-3-(4-(trifluoromethyl)phenyl)prop-2-en-1-olAusbeute 96 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

In 15 ml of toluene were dissolved 3.00 g (12.3 mmol) of ethyl trans-4-(trifluoromethyl)cinnamate, and 16.4 ml (24.6 mmol) of a 1.5M diisobutyl aluminum hydride-toluene solution were added to the solution with stirring at 0° C. After 20 minutes, ice-water was added to the reaction mixture and the mixture was stirred for 10 minutes, followed by removal of the insolubles by filtration using Celite. The filtrate was extracted with ethyl acetate and, after drying, the solvent was distilled off to obtain a crystalline residue. The residue was recrystallized from a mixed solvent of benzene-hexane to obtain 2.36 g (yield: 96%) of the title compound having a melting point of 53 to 55° C.

Aufarbeitung

  1. additionwere added to the solution
  2. stirringthe mixture was stirred for 10 minutes
  3. customfollowed by removal of the insolubles by filtration
  4. extractionThe filtrate was extracted with ethyl acetate
  5. customafter drying
  6. distillationthe solvent was distilled off
  7. customto obtain a crystalline residue
  8. customThe residue was recrystallized from a mixed solvent of benzene-hexane

Quellen und Nachweise

ORD-Eintrag
ord-a67ed009194843c88aac26d9700341f0
Quelldatensatz
uspto-grants-2001_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06306880B1

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