Potassium Hydroxide → 2-(4-Fluorophenyl)-2-methylpropanoic acid

HRID 2078054Notes

Reaction equation

HRID 2078054 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:15])([CH3:14])[C:9]([O:11]CC)=[O:10])=[CH:4][CH:3]=1.[OH-].[K+]>CCO.O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([CH3:15])([CH3:14])[C:9]([OH:11])=[O:10])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 62393957Ethyl 2-(4-fluorophenyl)-2-methylpropanoate

Product 1

HCID 201638032-(4-Fluorophenyl)-2-methylpropanoic acidYield 58.7%

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Procedure

A mixture of ethyl 2-(4-fluorophenyl)-2-methylpropanoate (6 g, 29 mmol), KOH (3 g, 57 mmol) and 100 mL EtOH/H2O (4:1) was refluxed for 4 hours. The mixture was cooled to room temperature. The mixture was extracted with EtOAc and the organic layer discarded. The water layer was acidified with concentrated HCl, extracted with EtOAc, washed with H2O and brine, dried over anhydrous Na2SO4, and concentrated in vacuo to give 3.1 g of the product as a white solid. MS m/e=211 (M−1)−.

Workup

  1. temperaturewas refluxed for 4 hours
  2. extractionThe mixture was extracted with EtOAc
  3. extractionextracted with EtOAc
  4. washwashed with H2O and brine
  5. dry with materialdried over anhydrous Na2SO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-47dba53d8d744b7cb13cbf8d7b484183
Source dataset
uspto-grants-2011_04
Patent number
US07928139B2

Reaction notes

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