Methanol → Methyl 4-chloro-2-hydroxybenzoate

HRID 1403370Notes

Reaction equation

HRID 1403370 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([OH:11])[CH:3]=1.S(Cl)(Cl)=O.[CH3:16]O>>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][CH3:16])=[O:7])=[C:4]([OH:11])[CH:3]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 787824-Chlorosalicylic acid

Product 1

HCID 327085Methyl 4-chloro-2-hydroxybenzoateYield 95%

Procedure

To a solution of 4-chloro-2-hydroxybenzoic acid (20 g, 115.90 mmol) in methanol (500 mL) was added thionyl chloride (26 mL). After refluxing for 3 h, the reaction mixture was concentrated under vacuum, dissolved in petroleum ether (300 mL) and filtered to give methyl 4-chloro-2-hydroxybenzoate as a white solid (21 g, 95%).

Workup

  1. temperatureAfter refluxing for 3 h
  2. concentrationthe reaction mixture was concentrated under vacuum
  3. dissolutiondissolved in petroleum ether (300 mL)
  4. filtrationfiltered

Sources & evidence

ORD record
ord-5a1348a9fca84f868cfbd92c02a77418
Source dataset
uspto-grants-2014_12
Patent number
US08912188B2

Reaction notes

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