Sodium Chloride → 4-(N-2-hydroxyethyl-N-ethylamino)cinnamaldehyde

HRID 727741

Reaktionsgleichung

Reaktionsgleichung von HRID 727741
C([O:4][CH2:5][CH2:6][N:7]([C:10]1[CH:17]=[CH:16][C:13]([CH:14]=O)=[CH:12][CH:11]=1)[CH2:8][CH3:9])(=O)C.[Br-].[O:19]1CCO[CH:20]1[CH2:24][P+](CCCC)(CCCC)CCCC.CC(C)([O-])C.[K+].[Cl-].[Na+]>CN(C)C=O.Cl.O>[OH:4][CH2:5][CH2:6][N:7]([C:10]1[CH:11]=[CH:12][C:13]([CH:14]=[CH:24][CH:20]=[O:19])=[CH:16][CH:17]=1)[CH2:8][CH3:9]

Komponenten

8

Edukt 4

HCID 5234Sodium ChlorideHCID 11458991Benzaldehyde, 4-[[2-(acetyloxy)ethyl]ethylamino]-HCID 22292430Tributyl(1,3-dioxolan-2-ylmethyl)phosphonium BromideHCID 23665647Potassium tert-butoxide

Produkt 1

HCID 544515964-(N-2-hydroxyethyl-N-ethylamino)cinnamaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 313Hydrochloric AcidLösungsmittelHCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel2×

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

To a solution of 235.3 g (1 mole) of 4-(N-2-acetoxyethyl-N-ethylamino)benzaldehyde in dimethylformamide is added 738.7 g (2.0 moles) of 1,3-dioxolan-2-ylmethyltributylphosphonium bromide in dimethylformamide, and the mixture is heated at 90° C. Potassium t-butoxide (224.4 g, 2.0 moles) is added, and heating is continued at 90° C. for 16 hours. After cooling to room temperature, the solution is poured into a seven-fold excess of water, the aqueous mixture is saturated with sodium chloride, and the solution is extracted with three portions of ether. The combined organics are dried over 4A sieves, filtered through cotton, and evaporated. The crude reaction product is dissolved in 3M HCl, and the reaction is stirred at room temperature for 16 hours. After neutralization with saturated sodium bicarbonate, the aqueous mixture is extracted with three portions of ether, and the combined organics are dried over 4A sieves, filtered through cotton, and evaporated to yield the cinnamaldehyde as an oil. The product is purified by flash chromatography (silica gel, 1:1 hexane:ethyl acetate).

Aufarbeitung

  1. temperatureheating
  2. temperatureAfter cooling to room temperature
  3. extractionthe solution is extracted with three portions of ether
  4. dry with materialThe combined organics are dried over 4A sieves
  5. filtrationfiltered through cotton
  6. customevaporated
  7. customThe crude reaction product
  8. extractionAfter neutralization with saturated sodium bicarbonate, the aqueous mixture is extracted with three portions of ether
  9. dry with materialthe combined organics are dried over 4A sieves
  10. filtrationfiltered through cotton
  11. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-1f00ca9f8c4144c39ac015b68705ffc5
Quelldatensatz
uspto-grants-1991_09
Patentnummer
US05044725

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