Methanol → Benzoic acid, 5-chloro-2-hydroxy-, methyl ester

HRID 1032831Notes

Reaction equation

HRID 1032831 reaction equation
S(Cl)(Cl)=O.[Cl:5][C:6]1[CH:14]=[C:10]([C:11]([OH:13])=[O:12])[C:9]([OH:15])=[CH:8][CH:7]=1.[CH3:16]O>>[Cl:5][C:6]1[CH:14]=[C:10]([C:11]([O:13][CH3:16])=[O:12])[C:9]([OH:15])=[CH:8][CH:7]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 94475-Chlorosalicylic AcidHCID 24386Thionyl Chloride

Product 1

HCID 77684Benzoic acid, 5-chloro-2-hydroxy-, methyl ester

Procedure

To a cold solution of 100 ml methanol is slowly added 100 ml thionyl chloride followed by 30 g of 5-chlorosalicylic acid. This is then refluxed overnight, the solvent removed and the residue dissolved in ether. The ether is washed with a sodium bicarbonate solution, water, dried over magnesium sulfate and evaporated to dryness to obtain methyl 5-chlorosalicylate which is used directly in the next step.

Workup

  1. temperatureThis is then refluxed overnight
  2. customthe solvent removed
  3. dissolutionthe residue dissolved in ether
  4. washThe ether is washed with a sodium bicarbonate solution, water
  5. dry with materialdried over magnesium sulfate
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-5945bb8f2cbb4a77b03a99cb0de29369
Source dataset
uspto-grants-1990_09
Patent number
US04959485

Reaction notes

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