Ammonium Hydroxide → 2-CHLORO-4-HYDROXYPHENYLACETIC ACID

HRID 1602669Notes

Reaction equation

HRID 1602669 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([O:8]C)[CH:5]=[CH:4][C:3]=1[CH2:10][C:11]([OH:13])=[O:12].[OH-].[NH4+]>Br>[Cl:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[CH2:10][C:11]([OH:13])=[O:12]

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 42091322-(2-Chloro-4-methoxyphenyl)acetic acid

Product 1

HCID 196121452-CHLORO-4-HYDROXYPHENYLACETIC ACID

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Procedure

A solution of 1.6 g (8 mmol) of (2-chloro-4-methoxyphenyl)acetic acid, prepared according to Preparation 3, in 13 ml of hydrobromic acid (in 48% aqueous solution) is refluxed for two hours. After cooling, ammonium hydroxide is added until the pH is basic, and the mixture is extracted with methylene chloride. The water is evaporated from the aqueous phase and the residue is washed several times with ethanol to give the title compound.

Workup

  1. temperatureis refluxed for two hours
  2. temperatureAfter cooling
  3. extractionthe mixture is extracted with methylene chloride
  4. customThe water is evaporated from the aqueous phase
  5. washthe residue is washed several times with ethanol

Sources & evidence

ORD record
ord-aa6990d284b14c799dc46af6932b3928
Source dataset
uspto-grants-1999_11
Patent number
US05981754

Reaction notes

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