2,3-Dihydroxybenzoic Acid → Methyl 2,3-Dihydroxybenzoate

HRID 1626715Notes

Reaction equation

HRID 1626715 reaction equation
[OH:1][C:2]1[C:10]([OH:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].S(=O)(=O)(O)O.[CH3:17]O>>[CH3:17][O:5][C:4](=[O:6])[C:3]1[CH:7]=[CH:8][CH:9]=[C:10]([OH:11])[C:2]=1[OH:1]

Participants

4

Reactant 3

HCID 192,3-Dihydroxybenzoic AcidHCID 887MethanolHCID 1118Sulfuric Acid

Product 1

HCID 75484Methyl 2,3-Dihydroxybenzoate

Procedure

2,3-Dihydroxy-benzoic acid [A] (25 g, 0.16 mol) (Sigma-Aldrich, Cat no. 126209) was stirred in methanol (125 ml) with concentrated sulphuric acid (1 ml) and the reaction heated to gentle reflux over night. It was then concentrated and the residue partitioned between ethyl acetate and saturated aqueous sodium bicarbonate. The organic layer was washed with further saturated aqueous sodium bicarbonate, dried with magnesium sulphate, filtered and concentrated to afford 2,3-dihydroxy-benzoic acid methyl ester [B]. Yield 15.2 g, 57%.

Workup

  1. temperaturethe reaction heated
  2. temperatureto gentle reflux over night
  3. concentrationIt was then concentrated
  4. customthe residue partitioned between ethyl acetate and saturated aqueous sodium bicarbonate
  5. washThe organic layer was washed with further saturated aqueous sodium bicarbonate
  6. dry with materialdried with magnesium sulphate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-0fc2a4f77d2b439b9b028be09ef65bfa
Source dataset
uspto-grants-2014_07
Patent number
US08785457B2

Reaction notes

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