Methanol → Methyl 4-chloro-2-hydroxybenzoate

HRID 241577

Reaction equation

HRID 241577 reaction equation
S(=O)(=O)(O)O.[Cl:6][C:7]1[CH:8]=[C:9]([OH:16])[C:10](=[CH:14][CH:15]=1)[C:11]([OH:13])=[O:12].[CH3:17]O>>[Cl:6][C:7]1[CH:8]=[C:9]([OH:16])[C:10](=[CH:14][CH:15]=1)[C:11]([O:13][CH3:17])=[O:12]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 787824-Chlorosalicylic acid

Product 1

HCID 327085Methyl 4-chloro-2-hydroxybenzoateYield 83%

Procedure

5 ml of concentrated sulfuric acid is drop-added slowly to 100 ml of methanol. The solution is cooled and then added with a powder of 4-chloro-salicylic acid (17.20 g, 0.1 mol), and a reaction is carried out at reflux for 24 hours. After cooling the reaction, a large amount of deposit precipitates and is filtered out, washed with small amount of methanol, and recrystallized in anhydrous ethanol, to obtain 15.60 g of methyl 4-chloro-salicylate, with a yield of 83%.

Workup

  1. temperatureThe solution is cooled
  2. temperatureat reflux for 24 hours
  3. temperatureAfter cooling
  4. customthe reaction
  5. customa large amount of deposit precipitates
  6. filtrationis filtered out
  7. washwashed with small amount of methanol
  8. customrecrystallized in anhydrous ethanol

Sources & evidence

ORD record
ord-466b9f6184ea471992f1f153ca5427a2
Source dataset
uspto-grants-2014_02
Patent number
US08653069B2

Linked notes

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