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

HRID 1658593Notes

Reaction equation

HRID 1658593 reaction equation
[Cl:1][C:2]1[CH:10]=[C:6]([C:7]([OH:9])=[O:8])[C:5]([OH:11])=[CH:4][CH:3]=1.S(=O)(=O)(O)O.[CH3:17]O>>[Cl:1][C:2]1[CH:10]=[C:6]([C:7]([O:9][CH3:17])=[O:8])[C:5]([OH:11])=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 94475-Chlorosalicylic Acid

Product 1

HCID 77684Benzoic acid, 5-chloro-2-hydroxy-, methyl esterYield 92%

Procedure

5-Chlorosalicylic acid (5 kg.) dissolved in methanol (50 l.) and concentrated sulfuric acid (2 l.), was heated under reflux for 24 hours. The product crystallized when the solution was cooled in a dry ice/acetone mixture, and the solid when collected gave the ester (5 kg., 92%) sufficiently pure to use in the next step. Recrystallization give pure ester m.p. 45°-47°.

Workup

  1. temperatureunder reflux for 24 hours
  2. customThe product crystallized when the solution
  3. temperaturewas cooled in a dry ice/acetone mixture
  4. customthe solid when collected

Sources & evidence

ORD record
ord-ba797ae10ccc486a9e1cc34a59de5036
Source dataset
uspto-grants-1976_06
Patent number
US03965173

Reaction notes

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