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4-Hydroxybenzaldehyde → 4-(2-Methoxyethoxy)benzaldehyde

HRID 2214968
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2214968
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[I-].[K+].CC(C)([O-])C.[K+].[CH3:18][O:19][CH2:20][CH2:21]Cl>CN(C=O)C>[CH3:18][O:19][CH2:20][CH2:21][O:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 1264-HydroxybenzaldehydeHCID 4875Potassium IodideHCID 123162-Chloroethyl methyl etherHCID 23665647Potassium tert-butoxide

Produkt 1

HCID 64855604-(2-Methoxyethoxy)benzaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228Dimethylformamide
Lösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

146.5 g (1.2 mol) of 4-hydroxybenzaldehyde are dissolved in DMF, and 20 g (0.12 mol) of potassium iodide, 134.6 g (1.2 mol) of potassium tert-butoxide and 170.2 g (1.8 mol) of 2-chloroethyl methyl ether are added. The reaction mixture is stirred at 80° C. for 16 h. For work-up, the reaction mixture is concentrated under reduced pressure. The residue is taken up in 1 l of ethyl acetate and extracted with 0.5 l of 1N aqueous sodium hydroxide solution. The ethyl acetate phase is dried using magnesium sulphate and concentrated under reduced pressure. The residue obtained after concentration is distilled under high vacuum (b.p.=100° C. at 0.45 mbar). This gives 184.2 g (85% of theory) of product.

Aufarbeitung

  1. concentrationFor work-up, the reaction mixture is concentrated under reduced pressure
  2. extractionextracted with 0.5 l of 1N aqueous sodium hydroxide solution
  3. dry with materialThe ethyl acetate phase is dried
  4. concentrationconcentrated under reduced pressure
  5. customThe residue obtained
  6. concentrationafter concentration
  7. distillationis distilled under high vacuum (b.p.=100° C. at 0.45 mbar)

Quellen und Nachweise

ORD-Eintrag
ord-ceca3998d8a546c1a9ad185bb0a38d12
Quelldatensatz
uspto-grants-2006_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07109218B2

Notizen zur Reaktion

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