4-Hydroxybenzaldehyde → 4-(2-(5-Ethylpyridin-2-yl)-2-hydroxyethoxy)benzaldehyde

HRID 250150Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 250150
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:17][CH:18]([C:20]1[CH:25]=[CH:24][C:23]([CH2:26][CH3:27])=[CH:22][N:21]=1)[OH:19].O>C(O)(C)(C)C>[CH2:26]([C:23]1[CH:24]=[CH:25][C:20]([CH:18]([OH:19])[CH2:17][O:1][C:2]2[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=2)=[N:21][CH:22]=1)[CH3:27]

Komponenten

6

Edukt 4

HCID 1264-HydroxybenzaldehydeHCID 962WaterHCID 11430Potassium CarbonateHCID 45095769HCID 45095769, Verbindung

Produkt 1

HCID 115507874-(2-(5-Ethylpyridin-2-yl)-2-hydroxyethoxy)benzaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6386tert-ButanolLösungsmittel2×

Versuchsvorschrift

Into a solution of 22.6 g (0.181 mol) of 4-hydroxy benzaldehyde dissolved in 75 mL tertiary butanol, was added 38.5 g (0.278 mol) of potassium carbonate in 10 min. Reaction mixture was refluxed for 1 hr. and 15 g (0.06 mol) of 2-bromo-1-(5-ethyl-pyridin-2-yl)-ethanol dissolved in 75 mL tertiary butanol was added slowly in one hr. Reaction mixture was refluxed further for 10 hr. and at 25° C. poured into excess of water. Product was extracted with toluene. Subsequent concentration under reduced pressure and purification gave the desired product. Yield of the product was 12.37 g (70%). m.p. 80° C.

Aufarbeitung

  1. customReaction mixture
  2. temperaturewas refluxed for 1 hr
  3. additionwas added slowly in one hr
  4. customReaction mixture
  5. temperaturewas refluxed further for 10 hr
  6. extractionProduct was extracted with toluene
  7. concentrationSubsequent concentration
  8. customunder reduced pressure and purification

Quellen und Nachweise

ORD-Eintrag
ord-8e2735fc94364497865da4d29dbae9e3
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07863300B2

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