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

HRID 1732915
Notes
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Reaction equation

HRID 1732915 reaction equation
[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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 74741-Chloro-4-nitrobenzeneHCID 14797Potassium HydroxideHCID 15731(1,1'-Biphenyl)-2,2'-diol

Product 1

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

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent
HCID 962
Water
Solvent

Conditions

Temperature
80 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-89a03c10c4d942c5aa9ebe610e6059cf
Source dataset
uspto-grants-1980_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04239880

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes