Methanol → 3-(3-Bromo-4-methoxyphenyl)propanoic acid

HRID 1455709Notes

Reaction equation

HRID 1455709 reaction equation
C([O:3][C:4](=[O:16])[CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[C:9]([Br:15])[CH:8]=1)C.[OH-].[K+].CO>O>[Br:15][C:9]1[CH:8]=[C:7]([CH2:6][CH2:5][C:4]([OH:16])=[O:3])[CH:12]=[CH:11][C:10]=1[O:13][CH3:14]

Participants

5

Reactant 3

HCID 887MethanolHCID 14797Potassium HydroxideHCID 69049487Ethyl 3-(3-bromo-4-methoxyphenyl)propanoate

Product 1

HCID 45476083-(3-Bromo-4-methoxyphenyl)propanoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

154 g (0.535 mol) of ethyl3-(3-bromo-4-methoxyphenyl)propanoate are mixed with 45 g (0.8 mol) of potassium hydroxide, 600 ml of methanol and 300 ml of water. The mixture is heated at reflux for 3 hours, and the methanol is then evaporated off. The solution obtained is washed with ether; the aqueous phase is acidified and extracted with ether. The organic phase is dried (Na2SO4), and the solvents are evaporated off: white solid (132.7 g; 96%).

Workup

  1. temperatureThe mixture is heated
  2. temperatureat reflux for 3 hours
  3. customthe methanol is then evaporated off
  4. customThe solution obtained
  5. washis washed with ether
  6. extractionextracted with ether
  7. dry with materialThe organic phase is dried (Na2SO4)
  8. customthe solvents are evaporated off

Sources & evidence

ORD record
ord-9249e0c98ee743babcb237339e0146da
Source dataset
uspto-grants-2009_01
Patent number
US07482484B2

Reaction notes

Loading…