Acetic Acid → 2-(4-Nitrophenyl)butyric acid

HRID 1074440

Reaction equation

HRID 1074440 reaction equation
[C:1]1([CH:7]([CH2:11][CH3:12])[C:8]([OH:10])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N+:13]([O-])([OH:15])=[O:14].C(O)(=O)C>S(=O)(=O)(O)O>[N+:13]([C:4]1[CH:5]=[CH:6][C:1]([CH:7]([CH2:11][CH3:12])[C:8]([OH:10])=[O:9])=[CH:2][CH:3]=1)([O-:15])=[O:14]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 944Nitric AcidHCID 70122-Phenylbutyric Acid

Product 1

HCID 240472-(4-Nitrophenyl)butyric acid

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
20 °C

Procedure

A solution of 33.9 g of 2-phenylbutyric acid in 340 ml of concentrated sulfuric acid was cooled to -10° C. with stirring. To this solution was added, dropwise, a mixture of 39.4 ml of 70% nitric acid and 170 ml of acetic acid at such a rate that the temperature was maintained below 0° C. The mixture was then warmed to 20° C. over a period of 1 hour and poured into ice water. The off-white solid which formed was separated by filtration, washed with ice water and sucked as dry as possible on the filter. The resultant solid was dissolved in chloroform, a water layer was separated, and the chloroform layer was dried over magnesium sulfate. The solvent was removed under reduced pressure to give a crude solid which was recrystallized from a mixture of hot toluene/hexane to give 2-(4-nitrophenyl)butyric acid.

Workup

  1. additionTo this solution was added
  2. temperaturewas maintained below 0° C
  3. customThe off-white solid which formed
  4. customwas separated by filtration
  5. washwashed with ice water
  6. customas dry as possible on the filter
  7. dissolutionThe resultant solid was dissolved in chloroform
  8. customa water layer was separated
  9. dry with materialthe chloroform layer was dried over magnesium sulfate
  10. customThe solvent was removed under reduced pressure
  11. customto give a crude solid which
  12. customwas recrystallized from a mixture of hot toluene/hexane

Sources & evidence

ORD record
ord-3eb341737a534e1094e366c069b689a8
Source dataset
uspto-grants-1983_07
Patent number
US04391818

Linked notes

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