2-Ethylphenol → 2-Ethyl-6-nitrophenol

HRID 400600

Reaktionsgleichung

Reaktionsgleichung von HRID 400600
[CH2:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[OH:9])[CH3:2].F[B-](F)(F)F.[O:15]=[N+:16]=[O:17]>C(#N)C>[CH2:1]([C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([N+:16]([O-:17])=[O:15])[C:4]=1[OH:9])[CH3:2]

Komponenten

4

Edukt 2

HCID 69972-EthylphenolHCID 11073463Nitronium tetrafluoroborate

Produkt 1

HCID 150363132-Ethyl-6-nitrophenolAusbeute 60 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A solution of 2-ethylphenol (2.44 g, 20 mmol) in 80 mL of anhydrous acetonitrile was treated with nitronium tetrafluoroborate (2.93 g, 22 mmols) in portions over a period of 5 minutes at −30° C. to −40° C. After 20 minutes, the mixture was quenched with ice, treated with cold water and extracted with three 100 mL portions of dichloromethane. The combined organic layers were washed with two 30 mL portions of water, dried over sodium sulfate, filtered, and concentrated in vacuo. Chromatography on SiO2 (20% ethyl acetate in hexanes) gave 2.0 g of 2-ethyl-6-nitrophenol as a yellow oil (60% yield).

Aufarbeitung

  1. customthe mixture was quenched with ice
  2. additiontreated with cold water
  3. extractionextracted with three 100 mL portions of dichloromethane
  4. washThe combined organic layers were washed with two 30 mL portions of water
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-9ba1b52adac64ee2b33689d216471ae9
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08741897B2

Verknüpfte Notizen

Wird geladen…