Chloroacetic Acid → 2-(2-Acetyl-4-fluorophenoxy)acetic acid

HRID 2101444

Reaktionsgleichung

Reaktionsgleichung von HRID 2101444
Cl[CH2:2][C:3]([OH:5])=[O:4].[CH3:6][C:7]([C:9]1[CH:14]=[C:13]([F:15])[CH:12]=[CH:11][C:10]=1[OH:16])=[O:8].[OH-].[Na+]>O>[C:7]([C:9]1[CH:14]=[C:13]([F:15])[CH:12]=[CH:11][C:10]=1[O:16][CH2:2][C:3]([OH:5])=[O:4])(=[O:8])[CH3:6]

Komponenten

5

Edukt 3

HCID 300Chloroacetic AcidHCID 14798Sodium HydroxideHCID 959922-Acetyl-4-fluorophenol

Produkt 1

HCID 116585522-(2-Acetyl-4-fluorophenoxy)acetic acidAusbeute 61,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

Chloroacetic acid (99.3 mmol, 9.4 g) was added to a suspension of 5-fluoro-2-hydroxy acetophenone (33.1 mmol, 5.1 g) in water (60 mL) containing sodium hydroxide (165.4 mmol, 6.6 g) and the reaction mixture was refluxed for 3.5 hours. The reaction mixture was cooled to room temperature, poured into a separatory funnel and the oily liquid at the bottom of the funnel was discarded. The aqueous top layer was collected, cooled to 0° C. and acidified with conc. HCl. The white precipitate was collected, and air died. The dry solid was crystallized from toluene to obtain (2-acetyl-4-fluoro-phenoxy)-acetic acid, (57%, 4.3 g).

Aufarbeitung

  1. temperaturethe reaction mixture was refluxed for 3.5 hours
  2. additionpoured into a separatory funnel
  3. customThe aqueous top layer was collected
  4. temperaturecooled to 0° C.
  5. customThe white precipitate was collected
  6. customThe dry solid was crystallized from toluene

Quellen und Nachweise

ORD-Eintrag
ord-19ee35e26a9a43bcbe21bed4e83992a2
Quelldatensatz
uspto-grants-2009_08
Patentnummer
US07572910B2

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