Methanol → Methyl 2-hydroxy-6-methoxybenzoate

HRID 988284

Reaction equation

HRID 988284 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-867682a462d647e6b382d695393bf0f8
Source dataset
uspto-grants-2003_10
Patent number
US06635655B1

Linked notes

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