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Potassium Carbonate → Ethyl 4-[4-(4-trifluoromethylphenoxy)phenoxy]-2-pentenoate

HRID 2286680
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2286680
[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]([CH:27](Br)[CH3:28])[CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23].C(=O)([O-])[O-].[K+].[K+]>C(O)C>[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:27]([CH3:28])[CH:20]=[CH:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:12][CH:13]=2)=[CH:5][CH:4]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 170230p-(4-(Trifluoromethyl)phenoxy)phenolHCID 12922552Ethyl 3,4-dibromopentanoate

Produkt 1

HCID 156921Ethyl 4-[4-(4-trifluoromethylphenoxy)phenoxy]-2-pentenoateAusbeute 82 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel2×

Versuchsvorschrift

In a reactor, 30 g of ethanol was charged and 12.7 g (0.05 mole) of 4-(4-trifluoromethylphenoxy)phenol, 15.8 g (0.055 mole) of ethyl 3,4-dibromopentanoate, 8.7 g (0.063 mole) of potassium carbonate were charged. They were refluxed for 6 hours to react them. After the reaction, ethanol was distilled off from the reaction mixture and then 50 ml of toluene was added to the resulting mixture, and resulting solution was washed with water and then, the organic phase was washed with 5% hydrochloric acid and with water and then ethyl 3,4-dibromopentanoate and a lower boiling by-products were distilled off at 100° C. under a reduced pressure of 0.02-0.05 mmHg to obtain 15.6 g of ethyl 4-[4-(4-trifluoromethylphenoxy)phenoxy]-2-pentenoate (nD20 1.5175). The yield was 82.0%. The same process was repeated to obtain same compound except using ethyl 3,4-dichloropentanoate 10.9 g (0.055 mole) instead of ethyl 3,4-dibromopentanoate 15.8 g (0.055 mole). The yield was 73.6%.

Aufarbeitung

  1. temperatureThey were refluxed for 6 hours
  2. customto react them
  3. distillationwas distilled off from the reaction mixture
  4. addition50 ml of toluene was added to the resulting mixture
  5. customresulting solution
  6. washwas washed with water
  7. washthe organic phase was washed with 5% hydrochloric acid and with water
  8. distillationethyl 3,4-dibromopentanoate and a lower boiling by-products were distilled off at 100° C. under a reduced pressure of 0.02-0.05 mmHg

Quellen und Nachweise

ORD-Eintrag
ord-1f9d297e08914e4691569c3e88bf165d
Quelldatensatz
uspto-grants-1981_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04267317

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