Sulfuric Acid → Methyl Gentisate

HRID 1769163Notes

Reaction equation

HRID 1769163 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.[C:17](=O)(O)[O-].[Na+]>CO>[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

5

Reactant 3

HCID 1118Sulfuric AcidHCID 34692,5-Dihydroxybenzoic acidHCID 516892Sodium Bicarbonate

Product 1

HCID 75077Methyl Gentisate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2,5-Dihydroxybenzoic acid, 30 grams (0.195 moles), was heated to reflux with 10 ml conc'd. sulphuric acid in 500 ml methanol for 72 hours. Then it was neutralized with solid sodium bicarbonate and striped in vacuo. The product was extracted with ethyl acetate and the organic extract was dried and stripped in vacuo to give 29.8 grams of methyl 2,5-dihydroxybenzoate of >90% purity.

Workup

  1. temperatureto reflux with 10 ml conc'd
  2. extractionThe product was extracted with ethyl acetate
  3. extractionthe organic extract
  4. customwas dried

Sources & evidence

ORD record
ord-6c2ee7d9cb5e422ca7a7baf0501cbf84
Source dataset
uspto-grants-1995_01
Patent number
US05380755

Reaction notes

Loading…