4-Nitrophenol → 3-(4-Nitrophenoxy)propionic acid

HRID 2200197Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2200197
[CH:1]1[C:6]([N+:7]([O-:9])=[O:8])=[CH:5][CH:4]=[C:3]([OH:10])[CH:2]=1.Cl[CH2:12][CH2:13][C:14]([OH:16])=[O:15]>C(O)C.[OH-].[K+]>[N+:7]([C:6]1[CH:5]=[CH:4][C:3]([O:10][CH2:12][CH2:13][C:14]([OH:16])=[O:15])=[CH:2][CH:1]=1)([O-:9])=[O:8]

Komponenten

5

Edukt 2

HCID 9804-NitrophenolHCID 78993-Chloropropionic acid

Produkt 1

HCID 3515353-(4-Nitrophenoxy)propionic acidAusbeute 35,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 14797Potassium HydroxideLösungsmittel

Versuchsvorschrift

Dissolve p-nitrophenol (11 g, 100 mmol), 3-chloropropanoic acid (14 g, 100 mmol) in a mixture of ethanol (100 mL) and 20% aqueous KOH solution (100 mL). Heat to reflux for 2 hrs, then adjust pH=1-3, extract with EtOAc (300 mL×3), combine the organic layers and wash with brine (300 mL×2), dry over anhydrous Na2SO4. Concentrate under reduced pressure to give the crude product. Purification by chromatography (silica gel, EtOAc:PE=1:4) affords the title compound (7.5 g, 14.9%). MS: (M+1): 212.1.

Aufarbeitung

  1. temperatureHeat
  2. temperatureto reflux for 2 hrs
  3. extractionextract with EtOAc (300 mL×3)
  4. washwash with brine (300 mL×2)
  5. dry with materialdry over anhydrous Na2SO4
  6. concentrationConcentrate under reduced pressure
  7. customto give the crude product
  8. customPurification by chromatography (silica gel, EtOAc:PE=1:4)

Quellen und Nachweise

ORD-Eintrag
ord-d079d68512244b5c86d543ec6a651807
Quelldatensatz
uspto-grants-2016_06
Patentnummer
US09359338B2

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