Potassium Hydroxide → 3-(2-Bromophenyl)butanoic acid

HRID 1585970Notes

Reaction equation

HRID 1585970 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]([CH3:15])[CH2:9][C:10]([O:12]CC)=[O:11].[OH-].[K+]>C(O)C.O>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]([CH3:15])[CH2:9][C:10]([OH:12])=[O:11]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 21217383Ethyl 3-(2-bromophenyl)-3-methylpropionate

Product 1

HCID 212173793-(2-Bromophenyl)butanoic acidYield 105.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of 28.04 g of ethyl 3-(2-bromophenyl)-3-methylpropionate (109.1 mmole) in ethanol (200 ml) and water (100 ml) was added 12.2 g of potassium hydroxide (218.2 mmole), and the mixture was heated under reflux for 5 hours. After the mixture was left standing at room temperature, it was concentrated to a half of the volume by distillation and diluted again with dilute hydrochloric acid. Dichloromethane was then added, and an aqueous ammonium chloride solution was added before extraction. The organic layer was dried over magnesium sulfate, and the solvent was removed by distillation to give 27.97 g of 3-(2-bromophenyl)-3-methylpropionic acid (quantitatively).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 5 hours
  3. waitAfter the mixture was left
  4. customstanding at room temperature
  5. concentrationit was concentrated to a half of the volume by distillation
  6. additiondiluted again with dilute hydrochloric acid
  7. additionDichloromethane was then added
  8. additionan aqueous ammonium chloride solution was added before extraction
  9. dry with materialThe organic layer was dried over magnesium sulfate
  10. customthe solvent was removed by distillation

Sources & evidence

ORD record
ord-0ff46ffac2a94c92a1c413651685f292
Source dataset
uspto-grants-1999_08
Patent number
US05942459

Reaction notes

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