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

HRID 1904018

Reaktionsgleichung

Reaktionsgleichung von HRID 1904018
[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]

Komponenten

5

Edukt 2

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

Produkt 1

HCID 240472-(4-Nitrophenyl)butyric acidAusbeute 69,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-317526029b04445fa39601065981cd24
Quelldatensatz
uspto-grants-1984_03
Patentnummer
US04439448

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