Protocatechuic Acid → Methyl 3,4-Dihydroxybenzoate

HRID 1728875Notes

Reaction equation

HRID 1728875 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[OH:11])[C:5]([OH:7])=[O:6].[CH3:12]O.S(=O)(=O)(O)O>O>[CH3:12][O:6][C:5](=[O:7])[C:4]1[CH:8]=[CH:9][C:10]([OH:11])=[C:2]([OH:1])[CH:3]=1

Participants

5

Reactant 3

HCID 72Protocatechuic AcidHCID 887MethanolHCID 1118Sulfuric Acid

Product 1

HCID 287064Methyl 3,4-Dihydroxybenzoate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 100 g of 3,4-dihydroxy benzoic acid, 600 ml methyl alcohol and 10 ml of concentrated sulfuric acid is heated at reflux for 18 hours. The reaction mixture is cooled to room temperature, poured into water and extracted with methylene chloride. The organic layer is washed with saturated sodium bicarbonate and sodium chloride, dried and concentrated in vacuo to give 50.6 g of the desired product.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 18 hours
  3. extractionextracted with methylene chloride
  4. washThe organic layer is washed with saturated sodium bicarbonate and sodium chloride
  5. customdried
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-dbd6de7982cc46e89eac075a5044b889
Source dataset
uspto-grants-1994_07
Patent number
US05328921

Reaction notes

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