3-Hydroxybenzaldehyde → 3-[2-(2-Methoxyethoxy)ethoxy]benzaldehyde

HRID 23655

Reaktionsgleichung

Reaktionsgleichung von HRID 23655
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6].C(=O)([O-])[O-].[K+].[K+].Br[CH2:17][CH2:18][O:19][CH2:20][CH2:21][O:22][CH3:23]>CC(C)=O>[CH3:23][O:22][CH2:21][CH2:20][O:19][CH2:18][CH2:17][O:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6]

Komponenten

5

Edukt 3

HCID 1013-HydroxybenzaldehydeHCID 11430Potassium CarbonateHCID 1235321-Bromo-3,6-dioxaheptane

Produkt 1

HCID 225743243-[2-(2-Methoxyethoxy)ethoxy]benzaldehydeAusbeute 19,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

A mixture of 3.66 g of 3-hydroxybenzaldehyde, 4.6 g of powdered potassium carbonate, and 5.5 g of 1-bromo-2-(2-methoxyethoxy)ethane in 40 ml of acetone is stirred and refluxed under nitrogen for 18 h, then cooled and filtered. The filtrate is concentrated under reduced pressure, and the residue partitioned between CH2Cl2 and 1N NaOH. The aqueous phase is extracted with two additional portions of CH2Cl2, and the combined organic extracts dried (MgSO4) and concentrated under reduced pressure. Flash chromatography of the residue on silica using 20% EtOAc in CH2Cl2 affords 1.32 g of the title compound as a pale yellow oil.

Aufarbeitung

  1. temperaturerefluxed under nitrogen for 18 h
  2. temperaturecooled
  3. filtrationfiltered
  4. concentrationThe filtrate is concentrated under reduced pressure
  5. customthe residue partitioned between CH2Cl2 and 1N NaOH
  6. extractionThe aqueous phase is extracted with two additional portions of CH2Cl2
  7. dry with materialthe combined organic extracts dried (MgSO4)
  8. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-a3e80b08b9594f99806af366d9dccee3
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06852731B2

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