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Phenol → 3-Phenoxy-3'-(m-phenoxyphenoxy)biphenyl

HRID 1076461
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1076461
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[K+].C1(C)C=CC=CC=1.Cl[C:18]1[CH:19]=[C:20]([C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([O:30][C:31]3[CH:36]=[CH:35][CH:34]=[C:33]([O:37][C:38]4[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=4)[CH:32]=3)[CH:25]=2)[CH:21]=[CH:22][CH:23]=1>COCCOCCOC.[Cu].O>[O:7]([C:22]1[CH:21]=[C:20]([C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([O:30][C:31]3[CH:36]=[CH:35][CH:34]=[C:33]([O:37][C:38]4[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=4)[CH:32]=3)[CH:25]=2)[CH:19]=[CH:18][CH:23]=1)[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 996PhenolHCID 1140TolueneHCID 14797Potassium HydroxideHCID 215369223-Chloro-3'-(m-phenoxyphenoxy)biphenyl

Produkt 1

HCID 215369323-Phenoxy-3'-(m-phenoxyphenoxy)biphenyl

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23978Copper
Katalysator
HCID 962WaterLösungsmittel
HCID 8150DiglymeLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A 500 ml. reaction flask equipped with stirrer, condenser and Dean-Stark trap was charged with 250 g. (2.66 moles) of phenol. This was heated with stirring at 100°C. while 56 g. (1.0 mole) of potassium hydroxide was added in increments. Toluene (50 ml.) was then added to the fluld mass and water azeotroped from the system. After all toluene and water had been removed, 150 ml. of diglyme was added together with 5.0 g. (0.05 mole) of cuprous chloride and 1.0 g. of copper powder. To this mixture 20 g. (0.053 mole) of 3-chloro-3'-(m-phenoxyphenoxy)biphenyl in diglyme was added over a 30 minute period. Diglyme was distilled from the mixture which was then heated at 240° for 18 hrs. On cooling the mixture was slurried in 200 ml. of ether and salts were filtered off. The ethereal solution was washed with 25% potassium hydroxide solution, water until neutral and then dried over magnesium sulfate. The ether was removed under vacuum and the resulting oil distilled to give 13.1 g. of the desired product, bp 248°-253° /0.06 mm., nD25 1.6474.

Aufarbeitung

  1. customreaction flask
  2. customequipped with stirrer, condenser
  3. additionDean-Stark trap was charged with 250 g
  4. temperatureThis was heated
  5. customazeotroped from the system
  6. customAfter all toluene and water had been removed
  7. additionof diglyme was added together with 5.0 g
  8. distillationDiglyme was distilled from the mixture which
  9. temperaturewas then heated at 240° for 18 hrs
  10. temperatureOn cooling the mixture
  11. filtrationof ether and salts were filtered off
  12. washThe ethereal solution was washed with 25% potassium hydroxide solution, water until neutral and
  13. dry with materialthen dried over magnesium sulfate
  14. customThe ether was removed under vacuum
  15. distillationthe resulting oil distilled
  16. customto give 13.1 g

Quellen und Nachweise

ORD-Eintrag
ord-20d65c4d6c314de682b4a446e8cb2c21
Quelldatensatz
uspto-grants-1976_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US03957666

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