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

HRID 261042

반응식

HRID 261042 반응식
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]

참가 물질

4

반응물 2

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

생성물 1

HCID 130642142,6-Bis(5-chloro-2-hydroxy-3-nitrobenzyl)-4-chlorophenol수율 18.8%

시약·촉매·용매 1

HCID 3007855Zincchloride촉매

실험 절차

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°.

후처리

  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

출처 및 근거

ORD 기록
ord-0524ba43ac304538b82d8305f8464917
출처 데이터셋
uspto-grants-1979_08
특허 번호
US04163801

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