Ethanol → 3-(2-Bromophenyl)butanoic acid

HRID 234074Notes

Reaction equation

HRID 234074 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].C(O)C.[OH-].[K+]>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 3

HCID 702EthanolHCID 14797Potassium HydroxideHCID 21217383Ethyl 3-(2-bromophenyl)-3-methylpropionate

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of ethyl 3-(2-bromophenyl)-3-methylpropionate (28.04 g, 109.1 mmole) in the mixture of ethanol (200 ml) and water (100 ml) was added potassium hydroxide (12.2 g, 218.2 mmole). The solution was heated under reflux for 5 hours, left standing overnight as it was, the solvent was removed to about half of its original amount, and dilute hydrochloric acid was added to the concentrate. To this mixture was added dichloromethane followed by an aqueous ammonium chloride solution, the layers were separated, and the organic layer was dried over magnesium sulfate. The solvent was removed by distillation under reduced pressure to give 3-(2-bromophenyl)-3-methylpropionic acid (27.97 g, quant.).

Workup

  1. temperatureThe solution was heated
  2. temperatureunder reflux for 5 hours
  3. waitleft
  4. customthe solvent was removed to about half of its original amount, and dilute hydrochloric acid
  5. additionwas added to the concentrate
  6. additionTo this mixture was added dichloromethane
  7. customthe layers were separated
  8. dry with materialthe organic layer was dried over magnesium sulfate
  9. customThe solvent was removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-1d5978a6178c4c8380f56f12d2549544
Source dataset
uspto-grants-1997_01
Patent number
US05594081

Reaction notes

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