3-Nitrotoluene → 2,2'-Dimethylbenzidine

HRID 1768510

반응식

HRID 1768510 반응식
[N+:1]([C:4]1[CH:5]=[C:6]([CH3:10])[CH:7]=[CH:8][CH:9]=1)([O-])=O.[OH-].[Na+]>[Zn].C(O)C>[CH3:10][C:6]1[CH:5]=[C:4]([NH2:1])[CH:9]=[CH:8][C:7]=1[C:7]1[CH:8]=[CH:9][C:4]([NH2:1])=[CH:5][C:6]=1[CH3:10]

참가 물질

5

반응물 2

HCID 74223-NitrotolueneHCID 14798Sodium Hydroxide

생성물 1

HCID 665372,2'-Dimethylbenzidine

시약·촉매·용매 2

HCID 23994Zinc촉매2회HCID 702Ethanol용매

실험 절차

A mixture of 40.0 grams, 0.30 moles, of m-nitrotoluene; 24 mL of a 20 percent aqueous solution of sodium hydroxide, and 120 mL ethanol is stirred and heated at gentle reflux. Zinc dust, 69.6 grams, is slowly added to keep the solution boiling without heating. Following addition of the zinc dust, the mixture is heated at reflux for about 4 hours. The hot mixture is filtered by suction, and the zinc residue is washed with ethanol. Concentrated hydrochloric acid is then slowly added to the filtrate. The precipitate formed is collected following filtration and redissolved in hot water. The aqueous solution is thereafter allowed to cool to room temperature and basified with a 20 percent aqueous solution of sodium hydroxide. The resulting DMB is an oil that is extracted with ethyl ether following its formation. Subsequent evaporation of the ethyl ether yields an oil containing 18.3 grams, 57.4 percent, of solids following cooling. Finally, the solid DMB is recrystallized from ethyl ether.

후처리

  1. additionA mixture of 40.0 grams, 0.30 moles
  2. temperatureheated at gentle reflux
  3. temperaturewithout heating
  4. temperaturethe mixture is heated
  5. temperatureat reflux for about 4 hours
  6. filtrationThe hot mixture is filtered by suction
  7. washthe zinc residue is washed with ethanol
  8. additionConcentrated hydrochloric acid is then slowly added to the filtrate
  9. customThe precipitate formed
  10. customis collected
  11. filtrationfiltration
  12. dissolutionredissolved in hot water
  13. extractionis extracted with ethyl ether following its formation
  14. customSubsequent evaporation of the ethyl ether
  15. customyields an oil
  16. additioncontaining 18.3 grams, 57.4 percent
  17. temperatureof solids following cooling
  18. customFinally, the solid DMB is recrystallized from ethyl ether

출처 및 근거

ORD 기록
ord-60b78d983f994b53950b7f40a0dc54bc
출처 데이터셋
uspto-grants-1995_01
특허 번호
US05378420

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