4,4'-Dihydroxybiphenyl → 4,4'-Bis(3-nitrophenoxy)biphenyl

HRID 231616

반응식

HRID 231616 반응식
O[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[N+]([C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([N+:24]([O-:26])=[O:25])[CH:19]=1)([O-])=O.[C:27](=[O:30])([O-])[O-].[K+].[K+]>CN(C)C=O>[N+:24]([C:20]1[CH:19]=[C:18]([CH:23]=[CH:22][CH:21]=1)[O:14][C:11]1[CH:12]=[CH:13][C:8]([C:5]2[CH:6]=[CH:7][C:2]([O:30][C:27]3[CH:23]=[CH:18][CH:19]=[C:20]([N+:24]([O-:26])=[O:25])[CH:21]=3)=[CH:3][CH:4]=2)=[CH:9][CH:10]=1)([O-:26])=[O:25]

참가 물질

5

반응물 3

HCID 71124,4'-DihydroxybiphenylHCID 74521,3-DinitrobenzeneHCID 11430Potassium Carbonate

생성물 1

HCID 66118144,4'-Bis(3-nitrophenoxy)biphenyl수율 99.5%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
65 °C

실험 절차

A 3 liter glass reaction vessel was charged with 186 grams (1.0 mol) of 4,4'-dihydroxybiphenyl, 438 grams (2.6 mols) of m-dinitrobenzene, 363 grams of potassium carbonate and 2,000 ml of N,N-dimethylformamide. The mixture was reacted at a temperature of 145°-150° C. for 16 hours. After completing the reaction, the resultant mixture was cooled and filtered to remove potassium nitrite. The solvent was distilled off from the filtrate under reduced pressure. The residue was cooled to 65° C., added with 2,000 ml of methanol and stirred for an hour. The resulted crystals were filtered, washed with water, washed with methanol and dried to obtain 426 grams (99.5% yield) of 4,4'-bis(3-nitrophenoxy)biphenyl as brown crystals.

후처리

  1. customThe mixture was reacted at a temperature of 145°-150° C. for 16 hours
  2. customthe reaction
  3. filtrationfiltered
  4. customto remove potassium nitrite
  5. distillationThe solvent was distilled off from the filtrate under reduced pressure
  6. additionadded with 2,000 ml of methanol
  7. filtrationThe resulted crystals were filtered
  8. washwashed with water
  9. washwashed with methanol
  10. customdried

출처 및 근거

ORD 기록
ord-ce659955b949483983e33552a15ad669
출처 데이터셋
uspto-grants-1989_07
특허 번호
US04847311

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