3-Hydroxybenzoic Acid → 2-Chloro-3-hydroxybenzoic acid

HRID 375461Notes

Reaction equation

HRID 375461 reaction equation
[Cl:1]Cl.[OH:3][C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][CH:12]=1)[C:7]([OH:9])=[O:8]>CO>[Cl:1][C:5]1[C:4]([OH:3])=[CH:12][CH:11]=[CH:10][C:6]=1[C:7]([OH:9])=[O:8]

Participants

4

Reactant 2

HCID 74203-Hydroxybenzoic AcidHCID 24526Chlorine

Product 1

HCID 156313402-Chloro-3-hydroxybenzoic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Chlorine gas (10.3 g; 147 mmol) was slowly bubbled through a cold solution of 20 g (145 mmol) of 3-hydroxy benzoic acid in 100 mL of methanol, under nitrogen, while maintaining the temperature below -60° C. After approximately thirty minutes, the chlorine gas was flushed out with nitrogen and the reaction mixture was allowed to warm to room temperature and diluted with 100 mL of water. The desired titled compound was isolated by recrystallization to provide a white solid. This solid was purified by recyrstallization from 50 mL of water followed by recrystallization from 130 mL of benzene containing 10 mL of acetone to provide the desired titled compound.

Workup

  1. temperaturewhile maintaining the temperature below -60° C
  2. waitAfter approximately thirty minutes
  3. customthe chlorine gas was flushed out with nitrogen
  4. additiondiluted with 100 mL of water

Sources & evidence

ORD record
ord-9689ccd8afaf481f8279326e750caadc
Source dataset
uspto-grants-1996_01
Patent number
US05484926

Reaction notes

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