Sodium Hydroxide → 3-(2-Bromophenyl)propionic acid

HRID 234076

Reaction equation

HRID 234076 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH2:9][C:10]([O:12]C)=[O:11].[OH-].[Na+]>C(O)C.O>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH2:9][C:10]([OH:12])=[O:11]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 15712815Methyl 3-(2-bromophenyl)propanoate

Product 1

HCID 3160103-(2-Bromophenyl)propionic acidYield 96.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of methyl 3-(2-bromophenyl)propionate (35.77 g) in ethanol (80.7 ml) was added at room temperature dropwise a solution of sodium hydroxide (11.77 g) in water (40 ml). After the reaction mixture was stirred under reflux for 2.5 hrs. and left standing for cooling, methanol was removed by distillation under reduced pressure, the residue was poured into ice-hydrochloric acid and stirred for 20 minutes. Crystalline precipitates were filtered, washed well with water, dried under reduced pressure to give the title compound (32.4 g).

Workup

  1. temperatureunder reflux for 2.5 hrs
  2. waitand left standing
  3. temperaturefor cooling
  4. custommethanol was removed by distillation under reduced pressure
  5. additionthe residue was poured into ice-hydrochloric acid
  6. stirringstirred for 20 minutes
  7. customCrystalline precipitates
  8. filtrationwere filtered
  9. washwashed well with water
  10. customdried under reduced pressure

Sources & evidence

ORD record
ord-aa64c040a29d4ca19be381a75352ec36
Source dataset
uspto-grants-1997_01
Patent number
US05594081

Linked notes

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