Methanol → Methyl 2-hydroxy-6-methoxybenzoate

HRID 892185

Reaction equation

HRID 892185 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]([OH:12])[C:8]=1[C:9]([OH:11])=[O:10].[CH3:13]O>S(=O)(=O)(O)O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]([OH:12])[C:8]=1[C:9]([O:11][CH3:13])=[O:10]

Participants

4

Reactant 2

HCID 887MethanolHCID 5915242-Hydroxy-6-methoxybenzoic acid

Product 1

HCID 527092Methyl 2-hydroxy-6-methoxybenzoate

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

A mixture of 6-methoxysalicylic acid (10.0 g, 59.5 mmol) in methanol (40 mL) and sulfuric acid (2 mL) is heated at reflux 48 h. Although some acid remains the reaction is concentrated to remove the methanol and partitioned between ethyl acetate and saturated sodium carbonate solution. The organic phase is separated and washed with sodium carbonate until no acid remains by TLC analysis. The organic phase is dried and concentrated to provide the title compound as a low melting solid.

Workup

  1. temperatureis heated
  2. temperatureat reflux 48 h
  3. concentrationis concentrated
  4. customto remove the methanol
  5. custompartitioned between ethyl acetate and saturated sodium carbonate solution
  6. customThe organic phase is separated
  7. washwashed with sodium carbonate until no acid
  8. customThe organic phase is dried
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-be9d3173ea9943d198c95c9532640032
Source dataset
uspto-grants-2006_02
Patent number
US07005440B1

Linked notes

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