Hydrochloric Acid → 3-(Furan-2-yl)-2-oxopropanoic acid

HRID 1184320Notes

Reaction equation

HRID 1184320 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][C:7](=[O:11])[C:8]([O-:10])=[O:9].[OH-].[Na+].Cl>>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][C:7](=[O:11])[C:8]([OH:10])=[O:9]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 20497773-(Furan-2-yl)-2-oxopropanoate

Product 1

HCID 20497783-(Furan-2-yl)-2-oxopropanoic acidYield 57.1%

Conditions

Temperature
90 °C

Procedure

To a 100 mL flask, 3-(furan-2-yl)-2-oxopropanoate (940 mg) along with 23 mL cold 6N NaOH was added. The insoluble mixture was stirred in a 90° C. bath for 5 min until dissolved. Cold 1N HCl was added until solution was acidic (approx 120 mL). Solution was extracted 2×50 mL EtOAc. Combined organic layers were washed with 40 mL brine and dried with Na2SO4. Solution was evaporated to yield 540 mg brown solid. Solid was further purified by reversed-phase high-performance liquid chromatography (HPLC) ramping from 97% aqueous trifluoroacetic acid (TFA) to acetonitrile (ACN).

Workup

  1. dissolutionuntil dissolved
  2. extractionSolution was extracted 2×50 mL EtOAc
  3. washCombined organic layers were washed with 40 mL brine
  4. dry with materialdried with Na2SO4
  5. customSolution was evaporated

Sources & evidence

ORD record
ord-58402d3bd7054c958ef2a273569df5de
Source dataset
uspto-grants-2014_03
Patent number
US08669103B2

Reaction notes

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