Hydrochloric Acid → alpha-(Methoxyimino)furan-2-acetic acid

HRID 530193

Reaktionsgleichung

Reaktionsgleichung von HRID 530193
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6](=O)[C:7]([OH:9])=[O:8].Cl.[CH3:12][O:13][NH2:14].C([O-])([O-])=O.[Na+].[Na+].Cl>CO>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6](=[N:14][O:13][CH3:12])[C:7]([OH:9])=[O:8]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 738462-Furylglyoxylic acidHCID 521874O-Methylhydroxylamine hydrochloride

Produkt 1

HCID 2724574alpha-(Methoxyimino)furan-2-acetic acidAusbeute 109 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A magnetically stirred mixture of 2-(furan-2-yl)-2-oxoacetic acid (5.0 g, 35.7 mmol), O-methylhydroxylamine hydrochloride (5.96 g, 71.4 mmol) and Na2CO3 (15.13 g, 143 mmol) in 100 mL of MeOH was refluxed for 2 hr. The reaction mixture was cooled to room temperature and concentrated HCl was added slowly until a pH of 2-3 was obtained. Most of the solvent was removed on the rotary evaporator and the residue was diluted with 50 mL of water and 100 mL of ether. Concentrated HCl was again added to give a pH of 2-3. The aqueous layer was extracted with 2×50 mL of ether. The combined organic layers were washed with 50 mL of a saturated solution of NaCl, dried (MgSO4) and solvent removed to give 6.58 g of crude 2-(furan-2-yl)-2-(methoxyimino)acetic acid as a viscous oil (crystals formed upon standing).

Aufarbeitung

  1. temperaturewas refluxed for 2 hr
  2. customwas obtained
  3. customMost of the solvent was removed on the rotary evaporator
  4. additionthe residue was diluted with 50 mL of water and 100 mL of ether
  5. additionConcentrated HCl was again added
  6. customto give a pH of 2-3
  7. extractionThe aqueous layer was extracted with 2×50 mL of ether
  8. washThe combined organic layers were washed with 50 mL of a saturated solution of NaCl
  9. dry with materialdried (MgSO4) and solvent
  10. customremoved
  11. customto give

Quellen und Nachweise

ORD-Eintrag
ord-77aa7e3f1ef04cb58f237f8f518aca08
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09353060B2

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