Biphenyl → Fenbufen

HRID 1659147Notes

Reaction equation

HRID 1659147 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[N+](C1C=CC=CC=1)([O-])=O.[C:14]1(=[O:20])[O:19][C:17](=[O:18])[CH2:16][CH2:15]1.[C:21]1([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>>[C:21]1([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH:26]=[CH:25][C:24]([C:14]([CH2:15][CH2:16][C:17]([OH:19])=[O:18])=[O:20])=[CH:23][CH:22]=1

Participants

5

Reactant 4

HCID 7095BiphenylHCID 7416NitrobenzeneHCID 7922Succinic anhydrideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 3335Fenbufen

Procedure

A 135 g. portion of aluminum chloride is dissolved in 500 ml. of nitrobenzene, the solution being held below 10°C. by external cooling. A finely ground mixture of 50 g. of succinic anhydride and 75 g. of biphenyl is added to the stirred solution, the temperature being held below 10°C. It is then held at room temperature for 4 days. After pouring the reaction mixture into a solution of 150 ml. of concentrated hydrochloric acid in one liter of ice water, the nitrobenzene is removed by steam distillation. The solid is collected, dissolved in 4 liters of 3% hot sodium carbonate solution, clarified and reprecipitated by the addition of excess 6N sulfuric acid solution. The crude product is collected, dried, and recrystallized from ethanol to give the pure product, melting point 185°-187°C.

Workup

  1. custombeing held below 10°C. by external cooling
  2. additionA finely ground mixture of 50 g
  3. custombeing held below 10°C
  4. additionAfter pouring the reaction mixture into a solution of 150 ml
  5. customof concentrated hydrochloric acid in one liter of ice water, the nitrobenzene is removed by steam distillation
  6. customThe solid is collected
  7. dissolutiondissolved in 4 liters of 3% hot sodium carbonate solution
  8. customreprecipitated by the addition of excess 6N sulfuric acid solution
  9. customThe crude product is collected
  10. customdried
  11. customrecrystallized from ethanol
  12. customto give the pure product, melting point 185°-187°C.

Sources & evidence

ORD record
ord-259beeb38cdb4662a9547f4f696d5883
Source dataset
uspto-grants-1976_06
Patent number
US03966960

Reaction notes

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