Dimethyl Sulfoxide → 1,3-Bis(4-formylphenoxy)-5-chlorobenzene

HRID 263530

Reaktionsgleichung

Reaktionsgleichung von HRID 263530
F[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[Cl:10][C:11]1[CH:12]=[C:13]([OH:18])[CH:14]=[C:15]([CH:17]=1)[OH:16].[C:19](=[O:22])([O-])[O-].[K+].[K+].CS(C)=O>C(OCC)(=O)C.O>[CH:6]([C:5]1[CH:8]=[CH:9][C:2]([O:16][C:15]2[CH:17]=[C:11]([Cl:10])[CH:12]=[C:13]([O:18][C:2]3[CH:9]=[CH:8][C:5]([CH:19]=[O:22])=[CH:4][CH:3]=3)[CH:14]=2)=[CH:3][CH:4]=1)=[O:7]

Komponenten

7

Edukt 4

HCID 679Dimethyl SulfoxideHCID 11430Potassium CarbonateHCID 680234-FluorobenzaldehydeHCID 945541,3-Benzenediol, 5-chloro-

Produkt 1

HCID 190384981,3-Bis(4-formylphenoxy)-5-chlorobenzeneAusbeute 32 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

p-Fluorobenzaldehyde (7.7 g), 5.9 g of 5-chlororesorcinol and 12.3 g of anhydrous potassium carbonate were added to 50 ml of dimethyl sulfoxide and stirred for 12 hours at 100° C. After completion of the reaction, 100 ml of water and 200 ml of ethyl acetate were added to carry out phase separation. After three times of washing with 50 ml of 10% sodium chloride aqueous solution and subsequent drying over anhydrous magnesium sulfate, the solvent was evaporated. The resulting oily material was subjected to silica gel column chromatography (hexane:ethyl acetate (7:1)) to obtain 3.5 g of 1,3-bis(4-formylphenoxy)-5-chlorobenzene.

Aufarbeitung

  1. additionwere added
  2. customphase separation
  3. washAfter three times of washing with 50 ml of 10% sodium chloride aqueous solution
  4. dry with materialsubsequent drying over anhydrous magnesium sulfate
  5. customthe solvent was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-e01cc9ccd90348c2825383fc5f394d19
Quelldatensatz
uspto-grants-1997_07
Patentnummer
US05643931

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