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

HRID 1061190Notes

Reaction equation

HRID 1061190 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 recrystallization 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-b12c743fb5af4ce5b50111d11cb55c7c
Source dataset
uspto-grants-2003_02
Patent number
US06525215B2

Reaction notes

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