Nitrobenzene → 4-(4'-Methoxy-biphenyl-4-yl)-4-oxo-butyric acid

HRID 1856513

Reaction equation

HRID 1856513 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.[C:15]1(=[O:21])[O:20][C:18](=[O:19])[CH2:17][CH2:16]1.[N+](C1C=CC=CC=1)([O-])=O.[Cl-].[Al+3].[Cl-].[Cl-]>>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:10]=[CH:11][C:12]([C:15](=[O:21])[CH2:16][CH2:17][C:18]([OH:20])=[O:19])=[CH:13][CH:14]=2)=[CH:5][CH:4]=1

Participants

5

Reactant 4

HCID 7416NitrobenzeneHCID 7922Succinic anhydrideHCID 119434-MethoxybiphenylHCID 6451240Aluminum(III) Chloride

Product 1

HCID 230052384-(4'-Methoxy-biphenyl-4-yl)-4-oxo-butyric acid

Procedure

A 50 g. portion of p-methoxybiphenyl and 30 g. of succinic anhydride are mixed in 600 ml. of nitrobenzene and cooled to about 5° C. A 73 g. portion of aluminum chloride is added in portions keeping the temperature at about 5° C. The mixture is then stirred for 15 hours and allowed to stand at room temperature. The mixture is poured into ice and then steam distilled until no more nitrobenzene comes over. The residue solidifies and is dissolved in 1,250 ml. of water containing 63 g. sodium carbonate. The solution is boiled with charcoal, filtered and the filtrate is chilled. The precipitate is filtered at room temperature and the gummy mixture is acidified with HCl and cooled. The precipitate is triturated with 50% acetic acid and the insoluble portion is recovered by filtration giving 4'-methoxy-γ-oxo-4-biphenyl-butyric acid.

Workup

  1. customat about 5° C
  2. customto stand at room temperature
  3. additionThe mixture is poured into ice
  4. distillationsteam distilled until no more nitrobenzene
  5. dissolutionis dissolved in 1,250 ml
  6. filtrationfiltered
  7. temperaturethe filtrate is chilled
  8. filtrationThe precipitate is filtered at room temperature
  9. temperaturecooled
  10. customThe precipitate is triturated with 50% acetic acid
  11. filtrationthe insoluble portion is recovered by filtration

Sources & evidence

ORD record
ord-9f0f3b11a4c348e29acc91cea719cd59
Source dataset
uspto-grants-1980_08
Patent number
US04219668

Linked notes

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