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Water → 2-(Methoxymethoxy)-5-(trifluoromethyl)benzaldehyde

HRID 1081874
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1081874
[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]([F:14])([F:13])[F:12])=[CH:7][CH:6]=1.[Li]CCCC.CN([CH:23]=[O:24])C.O>CCOCC>[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]([F:12])([F:13])[F:14])=[CH:7][C:6]=1[CH:23]=[O:24]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 962WaterHCID 6228DimethylformamideHCID 110090761-(Methoxymethoxy)-4-(trifluoromethyl)benzeneHCID 178418339Butyllithium

Produkt 1

HCID 233631132-(Methoxymethoxy)-5-(trifluoromethyl)benzaldehydeAusbeute 79 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283
Diethyl Ether
Lösungsmittel
2×

Versuchsvorschrift

To the solution of 4-(trifluoromethyl)phenyl methoxymethyl ether (5 g) in anhydrous ether (50 ml) was gradually added dropwise 1.6M n-BuLi (16.7 ml) at room temperature. After stirring at room temperature for 2 hours, the solution of DMF (4.13 ml) in anhydrous ether (20 ml) was added dropwise over 30 minutes, and the solution was stirred for 1 hour. To the reaction solution was added water, and the ether layer was separated. The ether layer is was washed with water and saturated sodium chloride solution, and dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure. The resulting residue was purified by chromatography on a silica gel column (methylene chloride:hexane=1:1), to give the title compound (4.49 g; 79%).

Aufarbeitung

  1. stirringthe solution was stirred for 1 hour
  2. customthe ether layer was separated
  3. washThe ether layer is was washed with water and saturated sodium chloride solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe solvent was removed under reduced pressure
  6. customThe resulting residue was purified by chromatography on a silica gel column (methylene chloride:hexane=1:1)

Quellen und Nachweise

ORD-Eintrag
ord-405fa717f88f46a289474d2af6aa8292
Quelldatensatz
uspto-grants-1996_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05587392

Notizen zur Reaktion

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