3-Hydroxybenzaldehyde → 3-(2,2,2-Trichloro-1-hydroxyethyl)phenol

HRID 1960094Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1960094
[Al].[Pb](Br)Br.[OH:5][C:6]1[CH:7]=[C:8]([CH:11]=[CH:12][CH:13]=1)[CH:9]=[O:10].[C:14](Cl)([Cl:17])([Cl:16])[Cl:15]>CN(C)C=O>[Cl:15][C:14]([Cl:17])([Cl:16])[CH:9]([C:8]1[CH:7]=[C:6]([OH:5])[CH:13]=[CH:12][CH:11]=1)[OH:10]

Komponenten

6

Edukt 4

HCID 1013-HydroxybenzaldehydeHCID 5943Carbon TetrachlorideHCID 24831Lead (II) bromideHCID 5359268Aluminum

Produkt 1

HCID 687485713-(2,2,2-Trichloro-1-hydroxyethyl)phenolAusbeute 91 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Aluminum (8.06 g, 0.3 mol) and lead bromide (3.7 g, 0.01 mmol) were added to a mixture of 3-hydroxy benzaldehyde (12.3 g, 0.1 mol) was mixed with 200 ml of dimethylformamide. Carbon tetrachloride (61.53 g, 0.4 mol) was slowly added thereto, the mixture was stirred at room temperature for 10 hours, and unreacted solid was filtered to remove therefrom. After sequentially adding 5% HCl, ethylacetate and water thereto, the mixture was extracted three times with ethyl acetate. The combined organic layer was dried over anhydrous magnesium sulfate, filtered and distilled. The resulting residue was subjected to column chromatography (ethyl acetate:n-hexane=1:4) to obtain the title compound (12.57 g, 91%).

Aufarbeitung

  1. filtrationunreacted solid was filtered
  2. customto remove
  3. additionAfter sequentially adding 5% HCl, ethylacetate and water
  4. extractionthe mixture was extracted three times with ethyl acetate
  5. dry with materialThe combined organic layer was dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. distillationdistilled

Quellen und Nachweise

ORD-Eintrag
ord-8a07bd8b52cc420d9a7b30a37fd6afd6
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08410302B2

Notizen zur Reaktion

Wird geladen…