Hydrochloric Acid → 4-Chloro-2-[(4-chlorophenyl)ethen-2-yl]phenol

HRID 2384314

Reaktionsgleichung

Reaktionsgleichung von HRID 2384314
[Cl:1][C:2]1[CH:9]=[C:6]([CH:7]=O)[C:5]([OH:10])=[CH:4][CH:3]=1.[Cl-].[Cl:12][C:13]1[CH:38]=[CH:37][C:16](C[P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[CH:15][CH:14]=1.[C:39](=O)([O-])[O-].[K+].[K+].Cl>O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:10])=[C:6]([C:7]([C:16]2[CH:37]=[CH:38][C:13]([Cl:12])=[CH:14][CH:15]=2)=[CH2:39])[CH:9]=1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 124815-Chloro-salicylaldehydeHCID 2733546(4-Chlorobenzyl)triphenylphosphonium chloride

Produkt 1

HCID 666573014-Chloro-2-[(4-chlorophenyl)ethen-2-yl]phenolAusbeute 8,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

5-Chlorosalicylaldehyde (313 mg, 2 mmol) and 4-chlorobenzyltriphenyl-phosphonium chloride (847 mg, 2 mmol) were dissolved in N,N-dimethylfomamide (20 mL). Potassium carbonate (1.382 g, 10 mmol) dissolved in water (10 mL) was added, and the mixture was refluxed for 5 hours. After cooling, the reaction mixture was poured into 2 N hydrochloric acid and extracted with ethyl acetate. After the organic layer was washed with water and brine, dried over anhydrous magnesium sulfate, the residue obtained by evaporation under reduced pressure was purified by chromatography on silica gel (n-hexane:ethyl acetate=3:1) to give the title compound (44.6 mg, 8.4%) as a light gray solid.

Aufarbeitung

  1. additionwas added
  2. temperaturethe mixture was refluxed for 5 hours
  3. temperatureAfter cooling
  4. extractionextracted with ethyl acetate
  5. washAfter the organic layer was washed with water and brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customthe residue obtained by evaporation under reduced pressure
  8. customwas purified by chromatography on silica gel (n-hexane:ethyl acetate=3:1)

Quellen und Nachweise

ORD-Eintrag
ord-bae8e0dc97544650a17bb407d4727054
Quelldatensatz
uspto-grants-2012_09
Patentnummer
US08263657B2

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