Methanol → Methyl 3-hydroxy-4-methoxybenzoate

HRID 1934969Notes

Reaction equation

HRID 1934969 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

A solution of 30.8 g (183 mmol) of 3-hydroxy-4-methoxybenzoic acid and 6 mL of conc sulfuric acid in 600 mL of methanol was refluxed overnight. Most of the solvent was removed and the remaining solution was poured into 600 mL of water containing 25 g of sodium bicarbonate. The product was extracted into ether, treated with Darco, dried and evaporated. The yield was 31.8 g of methyl 3-hydroxy-4-methoxybenzoate as pale yellow crystals.

Workup

  1. customMost of the solvent was removed
  2. additionthe remaining solution was poured into 600 mL of water containing 25 g of sodium bicarbonate
  3. extractionThe product was extracted into ether
  4. additiontreated with Darco
  5. customdried
  6. customevaporated

Sources & evidence

ORD record
ord-8fccca71492f44c7869ce6a5059dfbed
Source dataset
uspto-grants-2002_05
Patent number
US06384051B1

Reaction notes

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