Sodium Hydroxide → 2-[3-(Trifluoromethyl)phenoxy]acetic acid

HRID 1929624Notes

Reaction equation

HRID 1929624 reaction equation
C[O:2][C:3](=[O:16])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([C:12]([F:15])([F:14])[F:13])[CH:7]=1.[OH-].[Na+]>CO>[F:13][C:12]([F:14])([F:15])[C:8]1[CH:7]=[C:6]([CH:11]=[CH:10][CH:9]=1)[O:5][CH2:4][C:3]([OH:16])=[O:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 13770364HCID 13770364, compound

Product 1

HCID 19914302-[3-(Trifluoromethyl)phenoxy]acetic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of (3-trifluoromethyl-phenoxy)-acetic acid methyl ester (7.220 g; 30.832 mmol) in MeOH (100 ml) was treated with aq. 1N NaOH (46.3 ml; 1.5 eq.), and the resulting mixture was further stirred at rt for 20 min. MeOH was then removed under reduced pressure, water (100 ml) was added followed by aq. 1N HCl (75 ml). Filtration of the precipitated solid, and drying under HV afforded (3-trifluoromethyl-phenoxy)-acetic acid as a colorless solid (6.020 g; 89%). LC-MS: tR=0.85 min.; [M+H]+: no ionisation.

Workup

  1. customMeOH was then removed under reduced pressure, water (100 ml)
  2. additionwas added
  3. filtrationFiltration of the precipitated solid
  4. customdrying under HV

Sources & evidence

ORD record
ord-577609f8ff2240a2b02d30a68b4fc4bc
Source dataset
uspto-grants-2012_05
Patent number
US08188082B2

Reaction notes

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