Water → (E)-2-(4-Bromophenyl)-3-cyclohexylacrylic acid

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Reaktionsgleichung

C([O:3][C:4](=[O:20])[C:5]([C:13]1[CH:18]=[CH:17][C:16]([Br:19])=[CH:15][CH:14]=1)=[CH:6][CH:7]1[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1)C.C[O-].[Na+].O.[OH-].[Na+]>CO>[Br:19][C:16]1[CH:15]=[CH:14][C:13](/[C:5](=[CH:6]\[CH:7]2[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]2)/[C:4]([OH:20])=[O:3])=[CH:18][CH:17]=1

Komponenten

Reaktionsbedingungen

Temperatur: 50 °C

Versuchsvorschrift

Dissolve E/Z mixture of 2-(4-bromo-phenyl)-3-cyclohexyl-acrylic acid ethyl ester (158.9 g, 472 mmol) in methanol (800 mL) and add the solution to sodium methoxide in methanol (222 mL, 30%). Stir the reaction mixture at 50° C. for 72 h. Add water (17 mL) and 5 N aqueous sodium hydroxide solution (10 mL) and stir at 50° C. until all methyl ester is hydrolyzed (1-4,days). Add water and evaporate the methanol; Add ether (300 mL) and water (200 mL) and adjust the pH to a value of 1 with 1 N HCl. Separate the layers and extract the aqueous layer with ether. Dry the combined organic layers organic phase over sodium sulfate, filter and concentrate. Recrystallization of the residue in EtOAc affords the title compound as a white solid (93.3 g). MS (m/e): 309 (M+H).

Aufarbeitung

dissolutionDissolve
customAdd water and evaporate the methanol
customSeparate the layers
extractionextract the aqueous layer with ether
dry with materialDry the combined organic layers organic phase over sodium sulfate
filtrationfilter
concentrationconcentrate
customRecrystallization of the residue in EtOAc

Quellen und Nachweise

ORD-Eintrag: ord-763078bb8f624cc6b197a0b7c4b3e9a6
Quelldatensatz: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07576108B2

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