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

HRID 489141

Reaction equation

HRID 489141 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>>[OH:1][C:2]1[C:10]([OH:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([O:6][CH3:17])=[O:5]

Participants

4

Reactant 3

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

Product 1

HCID 75484Methyl 2,3-Dihydroxybenzoate

Procedure

A mixture of 2,3-dihydroxybenzoic acid (3.8 g, 24.6 mmol) in methanol (300 ml) was treated dropwise with conc. Sulfuric acid (4.2 g) and the resultant solution was heated at reflux temperature overnight. Upon cooling the solvent was evaporated and the residue poured into ice-water. The mixture was extracted with dichloromethane (3×50 ml) and the combined organic fractions dried (Na2SO4) and concentrated to yield a pale tan solid (4.05 g).

Workup

  1. temperatureat reflux temperature overnight
  2. temperatureUpon cooling the solvent
  3. customwas evaporated
  4. additionthe residue poured into ice-water
  5. extractionThe mixture was extracted with dichloromethane (3×50 ml)
  6. dry with materialthe combined organic fractions dried (Na2SO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-ee1b46de3f4c429aa2531db13f266d31
Source dataset
uspto-grants-2005_12
Patent number
US06977255B2

Linked notes

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