2-(5-Chloro-2-methoxyphenyl)acetic acid → 2-(5-Chloro-2-hydroxyphenyl)acetic acid

HRID 488758Notes

Reaction equation

HRID 488758 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:12]C)=[C:6]([CH2:8][C:9]([OH:11])=[O:10])[CH:7]=1>Br.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:12])=[C:6]([CH2:8][C:9]([OH:11])=[O:10])[CH:7]=1

Participants

4

Reactant 1

HCID 15040472-(5-Chloro-2-methoxyphenyl)acetic acid

Product 1

HCID 2441992-(5-Chloro-2-hydroxyphenyl)acetic acidYield 88.5%

Reagents, catalysts & solvents 2

HCID 260Hydrogen BromideSolventHCID 962WaterSolvent

Procedure

A solution of (5-chloro-2-methoxy-phenyl)-acetic acid (15.5 g, 77.5 mmol) in 48% aqueous hydrogen bromide was heated to reflux for 20 hours. The solution was cooled, diluted with water and extracted with diethyl ether. The organic layer was dried over magnesium sulfate, filtered and concentrated in vacuo. The crude product was purified by trituration in 2:1 methylene chloride:hexanes to give (5-chloro-2-hydroxy-phenyl)-acetic acid (12.8 g). This was dissolved in a solution of ethanol saturated with hydrochloric acid and stirred 12 hours. The reaction was concentrated in vacuo, then the crude product was dissolved in diethyl ether and washed with saturated aqueous sodium hydrogen carbonate. The organic layer was dried over magnesium sulfate, filtered and concentrated in vacuo to give the title compound (12.7 g).

Workup

  1. temperatureto reflux for 20 hours
  2. temperatureThe solution was cooled
  3. extractionextracted with diethyl ether
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by trituration in 2:1 methylene chloride

Sources & evidence

ORD record
ord-bdb962b4328248a1bd3bdcf6f7124ccf
Source dataset
uspto-grants-2005_12
Patent number
US06974817B2

Reaction notes

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