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1-Chloro-4-nitrobenzene → 2,2'-Bis(4-nitrophenoxy)-1,1'-biphenyl

HRID 2048978
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2048978
[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](Cl)=[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 74741-Chloro-4-nitrobenzeneHCID 14797Potassium HydroxideHCID 15731(1,1'-Biphenyl)-2,2'-diol

Produkt 1

HCID 143443692,2'-Bis(4-nitrophenoxy)-1,1'-biphenylAusbeute 15 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittel
HCID 962
Water
Lösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

37.2 g (0.2 mol) of 2,2'-dihydroxy-biphenyl and 63 g (0.4 mol) of p-nitrochlorobenzene are dissolved in 160 ml of dimethylsulphoxide (DMSO) in a sulphonation flask and the solution is warmed to 80° C. A solution of 26.4 g (0.4 mol) of 85% strength potassium hydroxide in 20 ml of water is then added dropwise, whilst stirring, and the reaction solution is subsequently further stirred for 3 hours at 100°-110° C. After cooling, the reaction solution is poured into ice water and the resulting precipitate is washed several times with water. The resulting crude product is then dried for 20 hours under a high vacuum at 70° C. and unconverted nitrochlorobenzene sublimes away during drying. The residue is recrystallised twice from ethanol. 12.4 g (15% of theory) of 2,2'-di-(p-nitrophenoxy)-biphenyl are obtained in the form of slightly yellowish crystals; melting point 158° C.

Aufarbeitung

  1. stirringthe reaction solution is subsequently further stirred for 3 hours at 100°-110° C
  2. temperatureAfter cooling
  3. washthe resulting precipitate is washed several times with water
  4. dry with materialThe resulting crude product is then dried for 20 hours under a high vacuum at 70° C.
  5. dry with materialunconverted nitrochlorobenzene sublimes away during drying
  6. customThe residue is recrystallised twice from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-44b22f45f1344b26ba5f8d37cd789667
Quelldatensatz
uspto-grants-1980_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04196144

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