Nitric Acid → 5'-Fluoro-2'-hydroxy-3'-nitroacetophenone

HRID 325744

Reaktionsgleichung

Reaktionsgleichung von HRID 325744
[CH3:1][C:2]([C:4]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:5]=1[OH:11])=[O:3].[N+:12]([O-])([OH:14])=[O:13].O>S(=O)(=O)(O)O>[CH3:1][C:2]([C:4]1[C:5]([OH:11])=[C:6]([N+:12]([O-:14])=[O:13])[CH:7]=[C:8]([F:10])[CH:9]=1)=[O:3]

Komponenten

5

Edukt 3

HCID 944Nitric AcidHCID 962WaterHCID 959922-Acetyl-4-fluorophenol

Produkt 1

HCID 27589845'-Fluoro-2'-hydroxy-3'-nitroacetophenone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1118Sulfuric AcidLösungsmittel2×

Reaktionsbedingungen

Temperatur
-20 °C

Versuchsvorschrift

5-Fluoro-2-hydroxyacetophenone (20.0 g) was dissolved in concentrated sulphuric acid (150 ml), and the mixture was cooled to -20° C. A mixture of concentrated nitric acid (17.0 ml; s.g. 1.42) in concentrated sulphuric acid (18.0 ml) was then added to it, dropwise with stirring, keeping the temperature of the reaction mixture between -15° and -5° C. The reaction mixture was then allowed to warm up to -5° C. and was poured into iced water (2 liters). The yellow precipitated product was filtered off and recrystallised from ethanol to give 5-fluoro-2-hydroxy-3-nitroacetophenone (11.9 g), m.p. 87°-90° C.

Aufarbeitung

  1. additionwas then added to it
  2. customthe temperature of the reaction mixture between -15° and -5° C
  3. temperatureto warm up to -5° C.
  4. filtrationThe yellow precipitated product was filtered off
  5. customrecrystallised from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-1cbee42d0ddd47a0969e630c7e489cba
Quelldatensatz
uspto-grants-1984_04
Patentnummer
US04442115

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