Water → (2-Hydroxyphenyl)acetic acid

HRID 1588401Notes

Reaction equation

HRID 1588401 reaction equation
Cl[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([OH:11])=[O:10].[OH2:12]>>[OH:12][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([OH:11])=[O:10]

Participants

3

Reactant 2

HCID 962WaterHCID 17124o-Chlorophenylacetic acid

Product 1

HCID 11970(2-Hydroxyphenyl)acetic acid

Procedure

The process of the invention is conveniently carried out by suspending an alkali metal hydroxide in an organic solvent and adding (2-chlorophenyl)acetic acid and a catalyst to this suspension. The reaction mixture is heated to a temperature above 130° C. The reaction can be followed by a chromatographic technique for (example gas/liquid chromatography or high pressure liquid chromatography (using reverse phase medium)) to follow its progress. When the reaction is complete the mixture is cooled and water is added to it. After washing the aqueous phase with a suitable solvent (for example, hexane) it is acidified and extracted with a suitable solvent (for example, ethyl acetate). The extracts are combined, dried and evaporated to leave crude (2-hydroxyphenyl)acetic acid which may be purified.

Workup

  1. temperatureThe reaction mixture is heated to a temperature above 130° C
  2. customThe reaction
  3. temperatureis cooled
  4. washAfter washing the aqueous phase with a suitable solvent (for example, hexane) it
  5. customdried
  6. customevaporated

Sources & evidence

ORD record
ord-1c85255dc3694970b7e5671cf2214352
Source dataset
uspto-grants-1993_06
Patent number
US05221772

Reaction notes

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