4-Chloro-2-nitrophenol → 2,6-Bis(5-chloro-2-hydroxy-3-nitrobenzyl)-4-chlorophenol

HRID 894227

Reaktionsgleichung

Reaktionsgleichung von HRID 894227
Cl[CH2:2][C:3]1[CH:8]=[C:7]([Cl:9])[CH:6]=[C:5]([CH2:10]Cl)[C:4]=1[OH:12].[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[C:16]([N+:21]([O-:23])=[O:22])[CH:15]=1>[Cl-].[Zn+2].[Cl-]>[Cl:13][C:14]1[CH:15]=[C:16]([N+:21]([O-:23])=[O:22])[C:17]([OH:20])=[C:18]([CH:19]=1)[CH2:2][C:3]1[CH:8]=[C:7]([Cl:9])[CH:6]=[C:5]([CH2:10][C:18]2[CH:19]=[C:14]([Cl:13])[CH:15]=[C:16]([N+:21]([O-:23])=[O:22])[C:17]=2[OH:20])[C:4]=1[OH:12]

Komponenten

4

Edukt 2

HCID 69804-Chloro-2-nitrophenolHCID 2411974-Chloro-2,6-bis(chloromethyl)phenol

Produkt 1

HCID 130642142,6-Bis(5-chloro-2-hydroxy-3-nitrobenzyl)-4-chlorophenolAusbeute 18,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3007855ZincchlorideKatalysator

Versuchsvorschrift

Zinc chloride (2 g) was added in small portions over 75 min to a melt of 2,6-bis(chloromethyl)-4-chlorophenol (1.2 g) and 4-chloro-2-nitrophenol (3 g) at a temperature of 120°. The mixture was stirred at this temperature for approximately 1 hr. The black product was extracted several times with acetone and the extract filtered to remove black inorganic material. The acetone was removed by distillation under reduced pressure and the residue chromatographed on silica gel. Elution with hexane containing 3% ethyl acetate gave unreacted 4-chloro-2-nitrophenol and elution with hexane containing 20% ethyl acetate gave the title compound (0.5 g) which was recrystallised from aqueous ethanol; m.p. 200°.

Aufarbeitung

  1. extractionThe black product was extracted several times with acetone
  2. filtrationthe extract filtered
  3. customto remove black inorganic material
  4. customThe acetone was removed by distillation under reduced pressure
  5. customthe residue chromatographed on silica gel
  6. washElution with hexane containing 3% ethyl acetate
  7. customgave unreacted
  8. wash4-chloro-2-nitrophenol and elution with hexane containing 20% ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-281e04f5322b4fdb92f1fec382e91f1e
Quelldatensatz
uspto-grants-1981_08
Patentnummer
US04282390

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