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

HRID 2357656Notes

Reaction equation

HRID 2357656 reaction equation
[Br: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+]>CO>[Br: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 11277257Ethyl 2-(4-bromophenyl)-2-methylpropanoate

Product 1

HCID 109336792-(4-Bromophenyl)-2-methylpropanoic acidYield 77.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 100 mL round-bottom flask was charged with ethyl 2-(4-bromophenyl)-2-methylpropanoate (0.670 g, 2.47 mmol) in 2.5 mL of MeOH. Potassium hydroxide (2.0 M, 2.47 mL, 4.94 mmol) was added at 0° C. The reaction was heated to reflux for 2 h. After cooling the reaction was extracted with ethyl acetate. The aqueous layer was acidified with 2M HCl and extracted with dichloromethane (3×). The combined organic layers were dried over sodium sulfate, filtered and concentrated to give 464 mg of 2-(4-bromophenyl)-2-methylpropanoic acid as a white solid.

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux for 2 h
  3. temperatureAfter cooling the reaction
  4. extractionwas extracted with ethyl acetate
  5. extractionextracted with dichloromethane (3×)
  6. dry with materialThe combined organic layers were dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-ca1931ac95094066853a929a7421d630
Source dataset
uspto-grants-2010_07
Patent number
US07759337B2

Reaction notes

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