Sodium Hydroxide → 2-(4-Nitrophenyl)butyric acid

HRID 1904018

Reaction equation

HRID 1904018 reaction equation
[CH2:1]([C:3]([C:14]1[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=1)(C(OCC)=O)[C:4]([O:6]CC)=[O:5])[CH3:2].[OH-].[Na+]>C(O)C.O>[N+:20]([C:17]1[CH:16]=[CH:15][C:14]([CH:3]([CH2:1][CH3:2])[C:4]([OH:6])=[O:5])=[CH:19][CH:18]=1)([O-:22])=[O:21]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 20465989Diethyl 2-ethyl-2-(4-nitrophenyl)malonate

Product 1

HCID 240472-(4-Nitrophenyl)butyric acidYield 69.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

In 150 ml of ethanol was dissolved 37.18 g (0.12 mole) of diethyl 2-ethyl-2-(4-nitrophenyl)malonate and a solution of 30.41 g (0.76 mole) of sodium hydroxide in 100 ml of water was added and then heated under reflux for 3 hours on an oil bath. After the solvent was distilled off in vacuo, the residue was dissolved in 200 ml of water and then extracted with 300 ml of ether. The ether layer was removed and the water layer was acidified with conc. hydrochloric acid and extracted again with ether. The ether layer was separated, washed with saturated sodium chloride solution and dried over magnesium sulfate. The ether was distilled off in vacuo to give 17.25 g (0.083 mole, 69% yield) of 2-(4-nitrophenyl)-n-butyric acid.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 3 hours on an oil bath
  3. distillationAfter the solvent was distilled off in vacuo
  4. dissolutionthe residue was dissolved in 200 ml of water
  5. extractionextracted with 300 ml of ether
  6. customThe ether layer was removed
  7. extractionextracted again with ether
  8. customThe ether layer was separated
  9. washwashed with saturated sodium chloride solution
  10. dry with materialdried over magnesium sulfate
  11. distillationThe ether was distilled off in vacuo

Sources & evidence

ORD record
ord-317526029b04445fa39601065981cd24
Source dataset
uspto-grants-1984_03
Patent number
US04439448

Linked notes

Loading…