Nitric Acid → Ethyl 2-(4-hydroxy-3-nitrophenyl)propanoate

HRID 660291Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 660291
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH3:14])[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:4][CH:3]=1.[N+:15]([O-])([OH:17])=[O:16]>C(O)(=O)C>[OH:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([CH3:14])[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:6][C:7]=1[N+:15]([O-:17])=[O:16]

Komponenten

4

Edukt 2

HCID 944Nitric AcidHCID 12785115Ethyl 2-(4-hydroxyphenyl)propanoate

Produkt 1

HCID 21444155Ethyl 2-(4-hydroxy-3-nitrophenyl)propanoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

Ethyl 2-(4-hydroxyphenyl)propanoate (275 mg, 1.42 mmol) in acetic acid (2 mL) was added nitric acid (60-62%, 300 mg, 2.86 mmol) at room temperature. The mixture was stirred for 1 hour at 50° C. and cooled to room temperature. The reaction mixture was poured into ice water (20 mL) and extracted with EtOAc. The organic layer was dried with MgSO4 and filtered. EtOAc was removed by evaporation. The residue was purified by column chromatography eluting with n-Hexane/EtOAc=6/1.

Aufarbeitung

  1. temperaturecooled to room temperature
  2. extractionextracted with EtOAc
  3. dry with materialThe organic layer was dried with MgSO4
  4. filtrationfiltered
  5. customEtOAc was removed by evaporation
  6. customThe residue was purified by column chromatography
  7. washeluting with n-Hexane/EtOAc=6/1

Quellen und Nachweise

ORD-Eintrag
ord-2ec9fac7e39048f9ae2d4034758b82db
Quelldatensatz
uspto-grants-2011_12
Patentnummer
US08084484B2

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