2,3-Dihydroxybenzoic Acid → Ethyl 2,3-dihydroxybenzoate

HRID 383904

Reaction equation

HRID 383904 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.[CH2:17](O)[CH3:18]>>[OH:1][C:2]1[C:10]([OH:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([O:6][CH2:17][CH3:18])=[O:5]

Participants

4

Reactant 3

HCID 192,3-Dihydroxybenzoic AcidHCID 702EthanolHCID 1118Sulfuric Acid

Product 1

HCID 2779843Ethyl 2,3-dihydroxybenzoateYield 100%

Procedure

To a solution of 2,3-dihydroxybenzoic acid (25 g) in ethanol (320 ml) was added concentrated sulfuric acid (1.8 ml), and the mixture was heated under reflux for one day. The reaction mixture was concentrated, poured into water, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over sodium sulfate. The solvent was evaporated under reduced pressure. The residue was subjected to normal phase chromatography (elution solvent ethyl acetate) to give the title compound (30 g, 100%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for one day
  3. concentrationThe reaction mixture was concentrated
  4. additionpoured into water
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe organic layer was washed with saturated brine
  7. dry with materialdried over sodium sulfate
  8. customThe solvent was evaporated under reduced pressure
  9. washThe residue was subjected to normal phase chromatography (elution solvent ethyl acetate)

Sources & evidence

ORD record
ord-e38d34a083614660b0d3bfd1ce15e04d
Source dataset
uspto-grants-2013_02
Patent number
US08367695B2

Linked notes

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