Dimethylformamide → HCID 3839920, Verbindung

HRID 1294097Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1294097
[CH2:1]([O:3][C:4]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][C:5]=1[CH:6]=[O:7])[CH3:2].[CH2:13](Br)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[CH2:13]([O:12][C:9]1[CH:10]=[CH:11][C:4]([O:3][CH2:1][CH3:2])=[C:5]([CH:8]=1)[CH:6]=[O:7])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 3572385HCID 3572385, Verbindung

Produkt 1

HCID 3839920HCID 3839920, VerbindungAusbeute 88,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

A mixture of 2-ethoxy-5-hydroxybenzaldehyde (3.72 g), benzyl bromide (5.75 g), anhydrous potassium carbonate (3.10 g) and N,N-dimethylformamide (50 mL) was stirred at 90° C. for 3 hrs. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated. The obtained residue was subjected to silica gel column chromatography to give crystals (5.06 g, 88%) of 5-benzyloxy-2-ethoxybenzaldehyde from a fraction eluted with ethyl acetate-hexane (1:4, v/v). Redrystallization from ethyl, acetate-hexane gave colorless prism crystals. melting point: 81-82° C.

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-2ccfae50c58e4bb69850306fd79b324f
Quelldatensatz
uspto-grants-2007_07
Patentnummer
US07238716B2

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