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

HRID 2048978
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인쇄 미리보기

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HRID 2048978 반응식
[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]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 962Water
용매

반응 조건

온도
80 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-44b22f45f1344b26ba5f8d37cd789667
출처 데이터셋
uspto-grants-1980_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04196144

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