Hydrochloric Acid → (E)-5-methyl-4-bis(4-fluorophenyl)methylidene-2-hexenoic acid

HRID 2380642Notizen

Reaktionsgleichung

[CH3:1][CH:2]([CH3:26])[C:3](=[C:11]([C:19]1[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=1)[C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=1)/[CH:4]=[CH:5]/[C:6]([O:8]CC)=[O:7].[OH-].[Na+].Cl>C1(C)C=CC=CC=1>[CH3:1][CH:2]([CH3:26])[C:3](=[C:11]([C:12]1[CH:13]=[CH:14][C:15]([F:18])=[CH:16][CH:17]=1)[C:19]1[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=1)/[CH:4]=[CH:5]/[C:6]([OH:8])=[O:7]

Komponenten

Reaktionsbedingungen

Temperatur: 60 °C

Versuchsvorschrift

A toluene (8 ml) solution of the above ester (2.38 g, 6.7 mmol) was added to powdery sodium hydroxide (0.34 g, 8.5 mmol) under argon atmosphere, and the whole was stirred at 60° C. for 5 hours. The reaction mixture was neutralized with 1M hydrochloric acid (10 ml) and extracted with ethyl acetate (25 ml×3 times). The organic layer was washed with water, saturated sodium chloride aq solution and then dried over anhydrous magnesium sulfate. Concentration of the organic layer in vacuo followed by recrystallization from a mixed solvent (hexane:ethyl acetate=4:1) gave 1.70 g (78% yield) of (E)-5-methyl-4-bis(4-fluorophenyl)methylidene-2-hexenoic acid. mp=225°-230° C. Rf =0.52 (hexane:ethyl acetate=1:1) IR (KBr): 3350, 2400, 3025, 1690, 1615, 1515, 1430, 1320, 1225, 1165, 1100, 1080, 1005, 965, 860, 850, 595, 580 cm-1.

Aufarbeitung

extractionextracted with ethyl acetate (25 ml×3 times)
washThe organic layer was washed with water, saturated sodium chloride aq solution
dry with materialdried over anhydrous magnesium sulfate
customConcentration of the organic layer in vacuo followed by recrystallization from a mixed solvent (hexane:ethyl acetate=4:1)

Quellen und Nachweise

ORD-Eintrag: ord-5b5687f8450141daa202ed89c2bd0268
Quelldatensatz: uspto-grants-1994_11
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US05369109

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