Methanol → Methyl 3-hydroxy-4-methoxybenzoate

HRID 1934722Notes

Reaction equation

HRID 1934722 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[O:11][CH3:12])[C:5]([OH:7])=[O:6].S(=O)(=O)(O)O.[CH3:18]O>>[OH:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[O:11][CH3:12])[C:5]([O:7][CH3:18])=[O:6]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 12575Isovanillic Acid

Product 1

HCID 4056967Methyl 3-hydroxy-4-methoxybenzoate

Procedure

To a solution of 3-hydroxy-4-methoxybenzoic acid (10.0 g) in methanol (100 mL) was added conc. sulfuric acid (10 mL) under ice-water cooling, and the mixture was heated for 15 hours under reflux. After evaporation of the solvent, the residue was partitioned between ethyl acetate and water. The separated organic layer was washed with an aqueous saturated sodium bicarbonate solution, water and brine. The resultant was dried over magnesium sulfate and evaporated in vacuo to give methyl 3-hydroxy-4-methoxybenzoate as a brown oil (9.43 g).

Workup

  1. temperaturethe mixture was heated for 15 hours
  2. temperatureunder reflux
  3. customAfter evaporation of the solvent
  4. customthe residue was partitioned between ethyl acetate and water
  5. washThe separated organic layer was washed with an aqueous saturated sodium bicarbonate solution, water and brine
  6. dry with materialThe resultant was dried over magnesium sulfate
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-a54f9496cfe74a8cbc60355c288fcf17
Source dataset
uspto-grants-2002_05
Patent number
US06384080B1

Reaction notes

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