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

HRID 250151Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 250151
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[H-].[Na+].Br[CH2:13][CH:14]([C:16]1[CH:21]=[CH:20][C:19]([CH2:22][CH3:23])=[CH:18][N:17]=1)[OH:15].O>CN(C)C=O>[CH2:22]([C:19]1[CH:20]=[CH:21][C:16]([CH:14]([OH:15])[CH2:13][O:1][C:2]2[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=2)=[N:17][CH:18]=1)[CH3:23]

Komponenten

6

Edukt 4

HCID 1264-HydroxybenzaldehydeHCID 962WaterHCID 24758Sodium hydrideHCID 45095769HCID 45095769, Verbindung

Produkt 1

HCID 115507874-(2-(5-Ethylpyridin-2-yl)-2-hydroxyethoxy)benzaldehydeAusbeute 68.918,102 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel3×

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

Into a solution of 9.635 kg (72.99 mol) of 4-hydroxy benzaldehyde dissolved in 50 lit. dimethylformamide was added 5.675 kg (236.45 mol) of sodium hydride in 5 lit. dimethylformamide and stirred for 15 min. To this was added 15 Kg (65.22 mol) of 2-bromo-1-(5-ethyl pyridin-2-yl)-ethanol dissolved in 500 lit dimethylformamide and stirring was continued for 1 hr. at 25 to 30° C. Reaction mixture was heated at 80 to 90° C. for 14 hr., allowed to cool to 25° C. and excess of water was added into it. Product was extracted with diethyl ether. Organic layer was dried (magnesium sulfate) and concentrated to obtain crude product, which was purified in methyl tert-butyl ether as described in example 17 to obtain 12,195 Kg (69%) pure 4-[2-(5-ethyl-pyridin-2-yl)-2-hydroxy-ethoxy]-benzaldehyde. m.p. 83° C.

Aufarbeitung

  1. dissolutiondissolved in 500
  2. stirringstirring
  3. waitwas continued for 1 hr
  4. customat 25 to 30° C
  5. customReaction mixture
  6. additionwas added into it
  7. extractionProduct was extracted with diethyl ether
  8. dry with materialOrganic layer was dried (magnesium sulfate)
  9. concentrationconcentrated
  10. customto obtain crude product, which
  11. customwas purified in methyl tert-butyl ether

Quellen und Nachweise

ORD-Eintrag
ord-16760148fed5461db91c984821a396db
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07863300B2

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