Oxalic Acid → HCID 15034422, compound

HRID 1073855Notes

Reaction equation

HRID 1073855 reaction equation
C([O:3][CH:4](OCC)[CH2:5][O:6][C:7]1[CH:12]=[C:11]([F:13])[CH:10]=[CH:9][C:8]=1[O:14][CH3:15])C.C(O)(=O)C(O)=O>CC(C)=O>[F:13][C:11]1[CH:10]=[CH:9][C:8]([O:14][CH3:15])=[C:7]([CH:12]=1)[O:6][CH2:5][CH:4]=[O:3]

Participants

4

Reactant 2

HCID 971Oxalic AcidHCID 15079980HCID 15079980, compound

Product 1

HCID 15034422HCID 15034422, compoundYield 30.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 23.0 g of 2-(5-fluoro-2-methoxyphenoxy)acetaldehyde diethylacetal in 130 ml of acetone were added 100 ml of 10% aqueous oxalic acid and the mixture was refluxed for 2 hours. After cooling, the reaction mixture was evaporated, and the residue was diluted with water and extracted with ether. The extract was washed with water, dried and evaporated. Isopropyl ether was added to the residue and the precipitate was filtered to give 4.99 g of the desired compound as pale brown crystals, which were recrystallized from a mixture of isopropanol and isopropyl ether as pale brown crystals, m.p. 92.5°-95° C.

Workup

  1. temperaturethe mixture was refluxed for 2 hours
  2. temperatureAfter cooling
  3. customthe reaction mixture was evaporated
  4. additionthe residue was diluted with water
  5. extractionextracted with ether
  6. washThe extract was washed with water
  7. customdried
  8. customevaporated
  9. additionIsopropyl ether was added to the residue
  10. filtrationthe precipitate was filtered

Sources & evidence

ORD record
ord-1952c50c855f453cb5d10af57b0d5218
Source dataset
uspto-grants-1990_11
Patent number
US04971990

Reaction notes

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