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p-Fluoronitrobenzene → 2,2'-Bis(4-nitrophenoxy)-1,1'-biphenyl

HRID 1732916
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1732916
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[OH:14].[N+:15]([C:18]1[CH:23]=[CH:22][C:21](F)=[CH:20][CH:19]=1)([O-:17])=[O:16].[OH-:25].[K+]>CS(C)=O.O>[N+:15]([C:18]1[CH:23]=[CH:22][C:21]([O:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[O:14][C:21]2[CH:22]=[CH:23][C:18]([N+:15]([O-:16])=[O:25])=[CH:19][CH:20]=2)=[CH:20][CH:19]=1)([O-:17])=[O:16]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 9590p-FluoronitrobenzeneHCID 14797Potassium HydroxideHCID 15731(1,1'-Biphenyl)-2,2'-diol

Produkt 1

HCID 143443692,2'-Bis(4-nitrophenoxy)-1,1'-biphenylAusbeute 77 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittel
HCID 962
Water
Lösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

18.62 g (0.1 mol) of 2,2'-dihydroxy-biphenyl and 28.22 g (0.2 mol) of p-nitrofluorobenzene are dissolved in 80 ml of dimethylsulphoxide in a sulphonation flask and the solution is warmed to 80° C. A solution of 13.2 g (0.2 mol) of 85% pure potassium hydroxide in 10 ml of water is then added dropwise, whilst stirring, and the reaction solution is subsequently further stirred for 3 hours at 100°-110° C. During this time a yellow precipitate forms and after the reaction mixture has cooled this is separated off by decanting off the supernatant liquor and is then washed several times with water. After drying, the crude product is recrystallised from ethanol. 32.86 g (77% of theory) of 2,2'-di-(p-nitrophenoxy)-biphenyl of analytical purity are obtained in the form of slightly yellowish crystals with a melting point of 158° C.

Aufarbeitung

  1. stirringthe reaction solution is subsequently further stirred for 3 hours at 100°-110° C
  2. temperatureDuring this time a yellow precipitate forms and after the reaction mixture has cooled
  3. customthis is separated off
  4. customby decanting off the supernatant liquor
  5. washis then washed several times with water
  6. customAfter drying
  7. customthe crude product is recrystallised from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-631bc70b45ed48c396d1eee6e418b407
Quelldatensatz
uspto-grants-1980_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04239880

Notizen zur Reaktion

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