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

HRID 22735

Reaction equation

HRID 22735 reaction equation
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]

Participants

5

Reactant 3

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

Product 1

HCID 116585522-(2-Acetyl-4-fluorophenoxy)acetic acidYield 61.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-13a18026d45547aba987540ce67c27c7
Source dataset
uspto-grants-2005_02
Patent number
US06849629B2

Linked notes

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