4'-Chloro-2-hydroxy-4-methoxybenzophenone → 2-[(E)-C-(4-chlorophenyl)-N-hydroxycarbonimidoyl]-5-methoxyphenol

HRID 568718Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 568718
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][C:10]=2[OH:17])=[CH:4][CH:3]=1.Cl.[NH2:20][OH:21]>N1C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5](/[C:8](=[N:20]\[OH:21])/[C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][C:10]=2[OH:17])=[CH:4][CH:3]=1

Komponenten

4

Edukt 2

HCID 665574'-Chloro-2-hydroxy-4-methoxybenzophenoneHCID 443297Hydroxyamine hydrochloride

Produkt 1

HCID 1364774242-[(E)-C-(4-chlorophenyl)-N-hydroxycarbonimidoyl]-5-methoxyphenol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

A mixture of 382 g of 4'-chloro-2-hydroxy-4-methoxybenzophenone, 230 g hydroxylamine hydrochloride and 1.5 liters of pyridine is heated under reflux for 3 hr. The solvent is evaporated and the residue is partitioned between hydrochloric acid and ethyl acetate. The organic extracts are combined and washed with saturated sodium chloride solution. The solvent is removed to afford a mixture of E- and Z-oxime isomers which is separated on a Waters Prep LC System 500 using 5% ethyl acetate/toluene as the eluting system to afford E-4'-chloro-2-hydroxy-4-methoxybenzophenone oxime, mp 159° C.

Aufarbeitung

  1. temperatureis heated
  2. temperatureunder reflux for 3 hr
  3. customThe solvent is evaporated
  4. customthe residue is partitioned between hydrochloric acid and ethyl acetate
  5. washwashed with saturated sodium chloride solution
  6. customThe solvent is removed
  7. customto afford
  8. customis separated on a Waters Prep LC System 500 using 5% ethyl acetate/toluene as the eluting system

Quellen und Nachweise

ORD-Eintrag
ord-784590844a3b48899b8f29094a83080e
Quelldatensatz
uspto-grants-1988_03
Patentnummer
US04728662

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