Hydrochloric Acid → [(3,6Dichloro-2methoxybenzoyl)aminooxy]acetic acid

HRID 568742Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 568742
[OH-].[Na+].[Cl:3][C:4]1[C:5]([O:15][CH3:16])=[C:6]([C:11]([Cl:14])=[CH:12][CH:13]=1)[C:7]([NH:9][OH:10])=[O:8].Br[CH2:18][C:19]([OH:21])=[O:20].Cl>O.C(O)C>[Cl:3][C:4]1[C:5]([O:15][CH3:16])=[C:6]([C:11]([Cl:14])=[CH:12][CH:13]=1)[C:7]([NH:9][O:10][CH2:18][C:19]([OH:21])=[O:20])=[O:8]

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 6227Bromoacetic AcidHCID 14798Sodium HydroxideHCID 140973413,6-Dichloro-2-methoxybenzohydroxamic acid

Produkt 1

HCID 14097342[(3,6Dichloro-2methoxybenzoyl)aminooxy]acetic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittel3×HCID 962WaterLösungsmittel3×

Versuchsvorschrift

To a solution of 86.34 g. of sodium hydroxide in 1.2 W of water was added 900 ml. of 95% ethanol and 240 g. of 3,6-dichloro-2-methoxybenzohydroxamic acid. To aid dissolution, an additional 300 ml. 95% ethanol and 60 ml. H2O were added. A solution of 153.12 g. bromoacetic acid in 120 ml. of 95% ethanol was then added to the reaction mixture over 0.5 hours, followed by 60 ml. of water. The mixture was then heated to reflux for 3 hours, cooled to ambient temperature, and 150 ml. 20% HCl added. The reaction mixture was then extracted twice with ethyl acetate. The ethyl acetate solutions were combined, washed with brine, and dried over MgSO4 overnight, then filtered and solvent evaporated in vacuo. The residue was crystallized from chloroform to yield [(3,6dichloro-2methoxybenzoyl)aminooxy]acetic acid as a white solid in two crops (m.p. 145°-154° C.).

Aufarbeitung

  1. dissolutiondissolution
  2. temperatureThe mixture was then heated
  3. temperatureto reflux for 3 hours
  4. extractionThe reaction mixture was then extracted twice with ethyl acetate
  5. washwashed with brine
  6. dry with materialdried over MgSO4 overnight
  7. filtrationfiltered
  8. customsolvent evaporated in vacuo
  9. customThe residue was crystallized from chloroform

Quellen und Nachweise

ORD-Eintrag
ord-d27e560c30324d8db906c19023318081
Quelldatensatz
uspto-grants-1988_03
Patentnummer
US04729781

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