Hydrochloric Acid → 4-[4-(4-Trifluoromethylphenoxy)phenoxy]-2-pentenoic acid

HRID 126971Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 126971
[F:1][C:2]([F:18])([F:17])[C:3]1[CH:16]=[CH:15][C:6]([O:7][C:8]2[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=2)=[CH:5][CH:4]=1.Br[CH:20]([CH3:26])[CH:21]=[CH:22][C:23]([O-:25])=[O:24].C(=O)([O-])[O-].[K+].[K+].[Br-].C([N+](CCCC)(CCCC)CC)CCC.Cl>O.ClC1C=CC=CC=1>[F:1][C:2]([F:17])([F:18])[C:3]1[CH:16]=[CH:15][C:6]([O:7][C:8]2[CH:9]=[CH:10][C:11]([O:14][CH:20]([CH3:26])[CH:21]=[CH:22][C:23]([OH:25])=[O:24])=[CH:12][CH:13]=2)=[CH:5][CH:4]=1

Komponenten

8

Edukt 5

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 170230p-(4-(Trifluoromethyl)phenoxy)phenolHCID 19043781N,N-Dibutyl-N-ethylbutan-1-aminium bromideHCID 736535464-Bromo-2-pentenoate

Produkt 1

HCID 1577944-[4-(4-Trifluoromethylphenoxy)phenoxy]-2-pentenoic acidAusbeute 91,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 7964ChlorobenzeneLösungsmittel

Versuchsvorschrift

In a reactor, 100 ml of chlorobenzene and 100 ml of water were charged and 95.3 g (0.375 mole) of 4-(4-trifluoromethylphenoxy)phenol, 73.7 g (0.412 mole) of 4-bromo-2-pentenoate, 78.0 g (0.56 mole) of potassium carbonate and 1.1 g (0.00375 mole) of tributylethylammonium bromide were added. The mixture was refluxed with stirring for 6 hours. The reaction mixture was cooled to the room temperature and conc. hydrochloric acid was added to the reaction mixture with stirring to be acidic. The water phase was separated and the organic phase was washed with water and chlorobenzene was distilled off at 100° C. under a reduced pressure of 0.02 to 0.05 mmHg to obtain 4-[4-(4-trifluoromethylphenoxy)phenoxy]-2-pentenoic acid. The yield was 91.2%.

Aufarbeitung

  1. temperatureThe mixture was refluxed
  2. additionwas added to the reaction mixture
  3. stirringwith stirring
  4. customThe water phase was separated
  5. washthe organic phase was washed with water and chlorobenzene
  6. distillationwas distilled off at 100° C. under a reduced pressure of 0.02 to 0.05 mmHg

Quellen und Nachweise

ORD-Eintrag
ord-059a3854385f4a3d9f174ddaf14b47ba
Quelldatensatz
uspto-grants-1981_03
Patentnummer
US04254262

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