Hydrochloric Acid → 2-(3-fluorophenoxy)-2-methylPropanoic acid

HRID 56275

Reaction equation

HRID 56275 reaction equation
[OH-].[K+].O.C([O:6][C:7](=[O:19])[C:8]([O:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=1)([CH3:10])[CH3:9])C.Cl>C(O)C>[F:18][C:14]1[CH:13]=[C:12]([CH:17]=[CH:16][CH:15]=1)[O:11][C:8]([CH3:10])([CH3:9])[C:7]([OH:19])=[O:6]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14797Potassium HydroxideHCID 58243746HCID 58243746, compound

Product 1

HCID 222707202-(3-fluorophenoxy)-2-methylPropanoic acidYield 61%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of KOH (2.38 g, 42.4 mmol) in mixed solvents of water (50 mL) and ethanol (70 mL) was added ethyl-2-(3-fluorophenoxy)-2-methylpropanoate (3.20 g, 14.1 mmol) in one portion and the mixture was stirred at 40° C. for 2 h. The mixture was cooled to 0° C., acidified to pH 3 with concentrated hydrochloric acid and extracted with DCM (20 mL×2). The combined organic layers were washed with brine (20 mL×2), dried over anhydrous Na2SO4 and concentrated in vacuo to give the title compound as a white solid (1.70 g, 61%).

Workup

  1. temperatureThe mixture was cooled to 0° C.
  2. extractionextracted with DCM (20 mL×2)
  3. washThe combined organic layers were washed with brine (20 mL×2)
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6f7369845df74bf493cc21caae373ac3
Source dataset
uspto-grants-2016_09
Patent number
US09434695B2

Linked notes

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