Methanol → Benzoic acid, 2-hydroxy-3-methyl-, methyl ester

HRID 1896159Notes

Reaction equation

HRID 1896159 reaction equation
[OH:1][C:2]1[C:10]([CH3:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].OS(O)(=O)=O.[CH3:17]O>>[CH3:17][O:5][C:4](=[O:6])[C:3]1[CH:7]=[CH:8][CH:9]=[C:10]([CH3:11])[C:2]=1[OH:1]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 67383-Methylsalicylic Acid

Product 1

HCID 31835Benzoic acid, 2-hydroxy-3-methyl-, methyl ester

Procedure

To a solution of 2-hydroxy-3-methyl-benzoic acid (10 g) in anh. MeOH (80 mL) was added dropwise H2SO4 (10.8 mL). The mixture was refluxed for 24 h and partitioned between DCM and water. The org. phase was separated, dried (Na2SO4) and evaporated off. The crude was purified by solid phase extraction to give the title product as a yellowish liquid (9.8 g).

Workup

  1. temperatureThe mixture was refluxed for 24 h
  2. custompartitioned between DCM and water
  3. customphase was separated
  4. dry with materialdried (Na2SO4)
  5. customevaporated off
  6. customThe crude was purified by solid phase extraction

Sources & evidence

ORD record
ord-78f8518a554f44ce884274b3fcbac5f5
Source dataset
uspto-grants-2013_08
Patent number
US08518912B2

Reaction notes

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