Methanol → Methyl Gentisate

HRID 1969161Notes

Reaction equation

HRID 1969161 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].S(=O)(=O)(O)O.[CH3:17]O>>[OH:1][C:2]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][C:3]=1[C:4]([O:6][CH3:17])=[O:5]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 34692,5-Dihydroxybenzoic acid

Product 1

HCID 75077Methyl Gentisate

Procedure

2,5-Dihydroxybenzoic acid (4 g) is dissolved in 20 mL of methanol. To the solution, 3 mL of concentrated sulfuric acid is added. The reaction mixture is brought to gentle reflux over 24 hours. Methanol is removed and the residue is diluted with water. The compound of interest is extracted into ethyl acetate. The organic layer is extracted with saturated sodium bicarbonate solution and dried over anhydrous sodium sulfate. Solvent is removed and the product is in the form of off-white powders.

Workup

  1. temperatureto gentle reflux over 24 hours
  2. customMethanol is removed
  3. additionthe residue is diluted with water
  4. extractionThe compound of interest is extracted into ethyl acetate
  5. extractionThe organic layer is extracted with saturated sodium bicarbonate solution
  6. dry with materialdried over anhydrous sodium sulfate
  7. customSolvent is removed

Sources & evidence

ORD record
ord-ccb49d93bc364780b07917eaa603bfb9
Source dataset
uspto-grants-2013_04
Patent number
US08426466B2

Reaction notes

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