Nitric Acid → 4-(4'-Nitro-4-biphenylyl)-butyric acid

HRID 2397383Notes

Reaction equation

HRID 2397383 reaction equation
[C:1]1([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:6]=[CH:5][C:4]([CH2:7][CH2:8][CH2:9][C:10]([OH:12])=[O:11])=[CH:3][CH:2]=1.[N+:19]([O-])([OH:21])=[O:20]>C(O)(=O)C>[N+:19]([C:16]1[CH:15]=[CH:14][C:13]([C:1]2[CH:6]=[CH:5][C:4]([CH2:7][CH2:8][CH2:9][C:10]([OH:12])=[O:11])=[CH:3][CH:2]=2)=[CH:18][CH:17]=1)([O-:21])=[O:20]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 111392304-{[1,1'-Biphenyl]-4-yl}butanoic acid

Product 1

HCID 214379364-(4'-Nitro-4-biphenylyl)-butyric acid

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a suspension of 14.4 gm of 4-(4-biphenylyl)-butyric acid in 72 ml of glacial acetic acid at 24°-27° C. 24 ml of fuming nitric acid (d=1.52) were added dropwise. After stirring for 5 minutes, the mixture was poured into ice water while stirring, and the aqueous mixture was extracted with benzene. The benzene phase was washed with water, dried and evaporated; the residue was dissolved in 100 ml of acetone and admixed with 6.8 ml of cyclohexylamine. The thus obtained cyclohexylamine salt had a melting point of 160°-161° C. (after recrystallization from 200 ml of isopropanol). Melting point of the free acid: 124° C. (from carbon tetrachloride).

Workup

  1. stirringwhile stirring
  2. extractionthe aqueous mixture was extracted with benzene
  3. washThe benzene phase was washed with water
  4. customdried
  5. customevaporated
  6. dissolutionthe residue was dissolved in 100 ml of acetone
  7. customa melting point of 160°-161° C. (after recrystallization from 200 ml of isopropanol)
  8. custom124° C. (from carbon tetrachloride)

Sources & evidence

ORD record
ord-0b79f8004f114b0991c2612b8bc4edbe
Source dataset
uspto-grants-1977_05
Patent number
US04021479

Reaction notes

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