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Hydrochloric Acid → Bis(2,4,6-trichlorophenyl) 2-[3-(trifluoromethyl)phenyl]propanedioate

HRID 341125
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 341125
[F:1][C:2]([F:19])([F:18])[C:3]1[CH:4]=[C:5]([CH:9]([C:14]([O:16][CH3:17])=[O:15])[C:10]([O:12][CH3:13])=[O:11])[CH:6]=[CH:7][CH:8]=1.[OH-].[Na+].[ClH:22].[Cl:23][C:24]1[CH:29]=[C:28]([Cl:30])[CH:27]=[C:26]([Cl:31])C=1O>O>[F:1][C:2]([F:18])([F:19])[C:3]1[CH:4]=[C:5]([CH:9]([C:10]([O:12][C:13]2[C:26]([Cl:31])=[CH:27][C:28]([Cl:30])=[CH:29][C:24]=2[Cl:23])=[O:11])[C:14]([O:16][C:17]2[C:24]([Cl:22])=[CH:29][C:28]([Cl:30])=[CH:27][C:26]=2[Cl:31])=[O:15])[CH:6]=[CH:7][CH:8]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 69142,4,6-TrichlorophenolHCID 14798Sodium HydroxideHCID 57348216Dimethyl-(3-(trifluoromethyl)-phenyl)-malonate

Produkt 1

HCID 86690526Bis(2,4,6-trichlorophenyl) 2-[3-(trifluoromethyl)phenyl]propanedioateAusbeute 50,43 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

The product of Step C was added to a solution of NaOH (25 g) in water (75 mL), and the reaction mixture was vigorously stirred under a nitrogen atmosphere at 60° C. for 8 minutes. The reaction mixture was then added to ice (100 g), and aqueous 6 N HCl was added until a pH of 1 was reached. The solution was extracted with ethyl acetate (3×100 mL), and the combined organic extracts were dried over magnesium sulfate, filtered, and concentrated under reduced pressure. Dichloromethane (200 mL) was added to the resulting white solid, followed by the addition of oxalyl chloride (5 mL) and N,N-dimethylformamide (0.5 mL). The reaction mixture was stirred at room temperature for 2 hours, followed by the addition of 2,4,6-trichlorophenol (10.528 g, 53.32 mmol). After stirring overnight at room temperature, the reaction mixture was concentrated under reduced pressure. Methanol was added to the resulting residue, and a solid slowly precipitated from the solution. The solid was collected by filtration to provide 8.161 g (50.43%) of the title product as a solid. 1H NMR (CDCl3) δ 7.91 (s, 1H), 7.83 (d, 1H), 7.70 (d, 1H), 7.59 (t, 1H), 7.37 (s, 4H), 5.38 (s, 1H).

Aufarbeitung

  1. additionwas added until a pH of 1
  2. extractionThe solution was extracted with ethyl acetate (3×100 mL)
  3. dry with materialthe combined organic extracts were dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. additionDichloromethane (200 mL) was added to the resulting white solid
  7. additionfollowed by the addition of oxalyl chloride (5 mL) and N,N-dimethylformamide (0.5 mL)
  8. stirringThe reaction mixture was stirred at room temperature for 2 hours
  9. stirringAfter stirring overnight at room temperature
  10. concentrationthe reaction mixture was concentrated under reduced pressure
  11. additionMethanol was added to the resulting residue
  12. customa solid slowly precipitated from the solution
  13. filtrationThe solid was collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-d743822888014dd5b072fb23035577f2
Quelldatensatz
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08895738B2

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