Ethanol → 5-(Ethoxycarbonyl)-2-hydroxybenzoic acid

HRID 423249Notes

Reaction equation

HRID 423249 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[C:11]([OH:13])=[O:12].S(=O)(=O)(O)O.C(=O)(O)[O-].[Na+].[CH2:24](O)[CH3:25]>>[CH2:24]([O:7][C:6](=[O:8])[C:5]1[CH:9]=[CH:10][C:2]([OH:1])=[C:3]([C:11]([OH:13])=[O:12])[CH:4]=1)[CH3:25]

Participants

5

Reactant 4

HCID 702EthanolHCID 1118Sulfuric AcidHCID 124904-Hydroxyisophthalic acidHCID 516892Sodium Bicarbonate

Product 1

HCID 539597625-(Ethoxycarbonyl)-2-hydroxybenzoic acid

Procedure

To a solution of 4-hydroxyisophthalic acid (10.0 g) in ethanol (100 mL) was added conc. sulfuric acid (3.0 mL), and the mixture was heated for 4 hours under reflux. The reaction solution was allowed to stand for cooling to room temperature, and poured into ice-water. Sodium bicarbonate was added thereto while stirring until the pH reached 10 to 11. The resulting precipitated solid was filtered off. To the filtrate was added conc. hydrochloric acid until the pH reached 2 to 3, and the precipitated solid was filtered off. The filtered solid was recrystallized from methanol and water (2:1, v/v) to give the title compound (4.53 g).

Workup

  1. temperaturethe mixture was heated for 4 hours
  2. temperatureunder reflux
  3. customThe resulting precipitated solid
  4. filtrationwas filtered off
  5. additionTo the filtrate was added conc. hydrochloric acid until the pH
  6. filtrationthe precipitated solid was filtered off
  7. customThe filtered solid was recrystallized from methanol and water (2:1

Sources & evidence

ORD record
ord-3b4e240a9dc44ef096111e17b402c4b5
Source dataset
uspto-grants-2012_01
Patent number
US08101774B2

Reaction notes

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