Hydrochloric Acid → Methyl 4-chloro-2-hydroxybenzoate

HRID 375062Notes

Reaction equation

HRID 375062 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[C:5]([OH:12])[C:6](=[CH:10][CH:11]=1)[C:7]([OH:9])=[O:8].[CH3:13]O>>[Cl:2][C:3]1[CH:4]=[C:5]([OH:12])[C:6](=[CH:10][CH:11]=1)[C:7]([O:9][CH3:13])=[O:8]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 787824-Chlorosalicylic acid

Product 1

HCID 327085Methyl 4-chloro-2-hydroxybenzoate

Procedure

Hydrogen chloride gas is bubbled into a mixture of 4-chlorosalicylic acid (100 g, 0.579 mol) in methanol while maintaining the temperature at 45°-50° C. The reaction mixture is then stirred at room temperature for several hours, concentrated in vacuo and extracted with ether. The combined organic extracts are washed sequentially with brine, saturated sodium hydrogen carbonate solution and brine, dried over anhydrous sodium sulfate and concentrated in vacuo to obtain an amber oil. The oil is distilled under reduced pressure to give the title product as a colorless oil which is identified by NMR spectral analyses.

Workup

  1. temperaturewhile maintaining the temperature at 45°-50° C
  2. concentrationconcentrated in vacuo
  3. extractionextracted with ether
  4. washThe combined organic extracts are washed sequentially with brine, saturated sodium hydrogen carbonate solution and brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customto obtain an amber oil
  8. distillationThe oil is distilled under reduced pressure

Sources & evidence

ORD record
ord-82a1bf7c55a840a0a8ccf38f075d70bd
Source dataset
uspto-grants-1996_01
Patent number
US05484763

Reaction notes

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