Hydrochloric Acid → (E)-4-(3-(3,5-dichlorophenyl)-4,4,4-trifluorobut-1-enyl)-2-methylbenzoic acid

HRID 587668Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 587668
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([C:24]([F:27])([F:26])[F:25])/[CH:10]=[CH:11]/[C:12]2[CH:22]=[CH:21][C:15]([C:16]([O:18]CC)=[O:17])=[C:14]([CH3:23])[CH:13]=2)[CH:5]=[C:6]([Cl:8])[CH:7]=1.Cl>O1CCOCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([C:24]([F:27])([F:25])[F:26])/[CH:10]=[CH:11]/[C:12]2[CH:22]=[CH:21][C:15]([C:16]([OH:18])=[O:17])=[C:14]([CH3:23])[CH:13]=2)[CH:5]=[C:6]([Cl:8])[CH:7]=1

Komponenten

4

Edukt 2

HCID 313Hydrochloric AcidHCID 86675123(E)-ethyl 4-(3-(3,5-dichlorophenyl)-4,4,4-trifluorobut-1-enyl)-2-methylbenzoate

Produkt 1

HCID 86675124(E)-4-(3-(3,5-dichlorophenyl)-4,4,4-trifluorobut-1-enyl)-2-methylbenzoic acidAusbeute 50 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a stirred solution of (E)-ethyl 4-(3-(3,5-dichlorophenyl)-4,4,4-trifluorobut-1-enyl) -2-methylbenzoate (1.7 g, 4.0 mmol) in 1,4-dioxane (10 mL) was added 11 N HCl (30 mL), and the reaction mixture was heated at 100° C. for 48 h. The reaction mixture was cooled to 25° C. and concentrated under reduced pressure. The residue was diluted with water and extracted with chloroform (CHCl3). The combined organic layer was dried over Na2SO4 and concentrated under reduced pressure, and the crude compound was washed with n-hexane to afford the title compound as a white solid (0.7 g, 50%): mp 142-143° C.; 1H NMR (400 MHz, DMSO-d6) δ 12.62 (br s, 1H), 7.81 (d, J=8.0 Hz, 1H), 7.66 (s, 3H), 7.52-7.44 (m, 2H), 6.89 (dd, J=16.0, 8.0 Hz, 1H), 6.78-6.74 (d, J=16.0 Hz, 1H), 4.84 (m, 1H), 2.50 (s, 3H); ESIMS m/z 387.05 ([M−H]−); IR (thin film) 3448, 1701, 1109, 777 cm−1.

Aufarbeitung

  1. temperatureThe reaction mixture was cooled to 25° C.
  2. concentrationconcentrated under reduced pressure
  3. additionThe residue was diluted with water
  4. extractionextracted with chloroform (CHCl3)
  5. dry with materialThe combined organic layer was dried over Na2SO4
  6. concentrationconcentrated under reduced pressure
  7. washthe crude compound was washed with n-hexane

Quellen und Nachweise

ORD-Eintrag
ord-9cd71d9be5ef45ad91e56559b3bc2c11
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09226501B2

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