Ethanol → 4-(3-Fluorophenoxy)butanoic acid

HRID 56251

Reaction equation

HRID 56251 reaction equation
[OH-].[K+].O.C(O)C.[F:7][C:8]1[CH:9]=[C:10]([CH:20]=[CH:21][CH:22]=1)[O:11][CH2:12][CH2:13][CH2:14][C:15]([O:17]CC)=[O:16]>C(Cl)Cl>[F:7][C:8]1[CH:9]=[C:10]([CH:20]=[CH:21][CH:22]=1)[O:11][CH2:12][CH2:13][CH2:14][C:15]([OH:17])=[O:16]

Participants

6

Reactant 4

HCID 702EthanolHCID 962WaterHCID 14797Potassium HydroxideHCID 21812847Ethyl 4-(3-fluoro-phenoxy)butanoate

Product 1

HCID 64860154-(3-Fluorophenoxy)butanoic acidYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of KOH (0.24 g, 4.28 mmol) in mixed solvents of water (3 mL) and ethanol (3 mL) under N2 was added ethyl 4-(3-fluorophenoxy)butanoate (0.30 g, 1.33 mmol) in one portion and the mixture was stirred at 40° C. for 4 h. It was then cooled to rt and 20 mL of DCM was added. The organic layer was washed with brine (20 mL×2), dried over anhydrous Na2SO4 and concentrated in vacuo to give the title compound as a white solid (0.25 g, 96%).

Workup

  1. temperatureIt was then cooled to rt
  2. washThe organic layer was washed with brine (20 mL×2)
  3. dry with materialdried over anhydrous Na2SO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-fdaf1e14d6bf43bcbc8ae6ddeb79e2ae
Source dataset
uspto-grants-2016_09
Patent number
US09434695B2

Linked notes

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