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

HRID 1732916Notes

Reaction equation

HRID 1732916 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](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]

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-631bc70b45ed48c396d1eee6e418b407
Source dataset
uspto-grants-1980_12
Patent number
US04239880

Reaction notes

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