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Dichloromethane → Methanone, 1,3-phenylenebis[(4-phenoxyphenyl)-

HRID 1885654
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1885654
[C:1]1([O:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:14](Cl)(=[O:24])[C:15]1[CH:23]=[CH:22][CH:21]=[C:17]([C:18](Cl)=[O:19])[CH:16]=1.C(Cl)Cl.[Cl-].[Al+3].[Cl-].[Cl-]>O>[O:7]([C:1]1[CH:2]=[CH:3][C:4]([C:14]([C:15]2[CH:23]=[CH:22][CH:21]=[C:17]([C:18](=[O:19])[C:11]3[CH:12]=[CH:13][C:8]([O:7][C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)=[CH:9][CH:10]=3)[CH:16]=2)=[O:24])=[CH:5][CH:6]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 6344DichloromethaneHCID 7451Isophthaloyl chlorideHCID 7583Diphenyl EtherHCID 6451240Aluminum(III) Chloride3×

Produkt 1

HCID 11070706Methanone, 1,3-phenylenebis[(4-phenoxyphenyl)-

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962
Water
Lösungsmittel

Reaktionsbedingungen

Temperatur
-5 °C

Versuchsvorschrift

Into a 2 liter flask equipped with a mechanical stirrer, thermometer, and nitrogen inlet and outlet, were charged 210 g (1.2338 moles) of diphenyl ether, 83.9 g (0.4132 moles) of isophthaloyl chloride, and 970 ml of methylene chloride. The solution was cooled to -5° C. by means of and acetone ice bath and then aluminum chloride (240 g, 1.8005 mole) was added in six 40 g portions. The temperature rose slightly during the addition of aluminum chloride and after the final addition the temperature was stabilized and held at 0° C. for thirty minutes. The solution was subsequently warmed to room temperature and held there for 1 hour. Afterwards, the solution was very slowly poured into agitated chilled demineralized water to deactivate the aluminum chloride (maximum water temperature reached was 28° C.). After stirring for 10 minutes, stirring was stopped and the very acidic upper layer was decanted off. The organic layer was subsequently washed several times with fresh dimeneralized water to remove the acid and filtered to remove solid impurities, e.g., elemental aluminum). Afterwards, methanol was slowly added to the organic layer (about 1/1 on a volume basis) with stirring and the product precipitated as short, white needles. Further purification was undertaken by slurrying 3X in isopropanol followed by filtration and drying. The short needles gave a DSC melting point (20° C./min) of 124° C.

Aufarbeitung

  1. customInto a 2 liter flask equipped with a mechanical stirrer
  2. additionafter the final addition the temperature
  3. waitheld at 0° C. for thirty minutes
  4. temperatureThe solution was subsequently warmed to room temperature
  5. additionAfterwards, the solution was very slowly poured
  6. stirringAfter stirring for 10 minutes
  7. stirringstirring
  8. customthe very acidic upper layer was decanted off
  9. customto remove the acid
  10. filtrationfiltered
  11. customto remove solid impurities, e.g., elemental aluminum)
  12. additionAfterwards, methanol was slowly added to the organic layer (about 1/1 on a volume basis)
  13. stirringwith stirring
  14. customthe product precipitated as short, white needles
  15. customFurther purification
  16. filtrationfollowed by filtration
  17. customdrying
  18. customThe short needles gave a DSC
  19. custompoint (20° C./min) of 124° C.

Quellen und Nachweise

ORD-Eintrag
ord-3641fbc9a9024b5c9e5cbdddc02b362e
Quelldatensatz
uspto-grants-1992_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05145899

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