Water → 4-Hydroxy-4'-chlorobenzophenone

HRID 225119

Reaktionsgleichung

Reaktionsgleichung von HRID 225119
[H-].[Na+].C(=N[OH:11])C1C=CC=CC=1.[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([C:19](=[O:29])[C:20]2[CH:25]=[CH:24][C:23]([N+]([O-])=O)=[CH:22][CH:21]=2)=[CH:15][CH:14]=1.O>CS(C)=O>[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([C:19](=[O:29])[C:20]2[CH:25]=[CH:24][C:23]([OH:11])=[CH:22][CH:21]=2)=[CH:15][CH:14]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 12143(Z)-Benzaldehyde oximeHCID 24758Sodium hydrideHCID 3477714-Chloro-4'-nitrobenzophenone

Produkt 1

HCID 1235044-Hydroxy-4'-chlorobenzophenone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel3×

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

250 cc of DMSO and 4.8 g sodium hydride are placed in a 500 cc flask and heated at 70° C. for 1 hour, by which time the solution has become clear. A solution of 24.2 g (0.2 mole) of benzaldoxime in 100 cc of DMSO is then added drop by drop. The solution is maintained at 70° C. for 1 hour, then allowed to cool to 15° C. A solution of 26 g (0.1 mole) of 4'-chloro-4-nitrobenzophenone in 150 cc of DMSO is then added. The reaction mixture is stirred for 20 hours at ambient temperature and then poured into acidulated water. The mixture is extracted with ether and then with ether containing 2 N caustic soda. On acidification the product is precipitated. Yield 15 g (65%). Melting point 178° C.

Aufarbeitung

  1. temperatureThe solution is maintained at 70° C. for 1 hour
  2. temperatureto cool to 15° C
  3. additionpoured
  4. extractionThe mixture is extracted with ether
  5. customOn acidification the product is precipitated

Quellen und Nachweise

ORD-Eintrag
ord-37898582841347cfa55f6a3527a44f0a
Quelldatensatz
uspto-grants-1980_11
Patentnummer
US04235896

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