Sodium Hydroxide → HCID 54231235, Verbindung

HRID 1534683Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1534683
[CH2:1]([C:8]1[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=1[CH:10]=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].[OH:16][C:17]1[CH:22]=[C:21]([O:23][CH2:24][CH:25]=[C:26]([CH3:28])[CH3:27])[CH:20]=[CH:19][C:18]=1[C:29](=[O:31])[CH3:30].[OH-].[Na+]>C(O)(C)C.O>[CH2:1]([C:8]1[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=1[CH:10]=[CH:30][C:29]([C:18]1[CH:19]=[CH:20][C:21]([O:23][CH2:24][CH:25]=[C:26]([CH3:28])[CH3:27])=[CH:22][C:17]=1[OH:16])=[O:31])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7]

Komponenten

6

Edukt 3

HCID 14798Sodium HydroxideHCID 109329682'-Hydroxy-4'-(3-methyl-2-butenyloxy)acetophenoneHCID 18417656HCID 18417656, Verbindung

Produkt 1

HCID 54231235HCID 54231235, VerbindungAusbeute 52,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 3776IsopropanolLösungsmittel

Reaktionsbedingungen

Temperatur
45 °C

Versuchsvorschrift

To a solution of 3.11 g of 2-heptylbenzaldehyde and 3.35 g of 2'-hydroxy-4'-(3-methyl-2-butenyloxy)-acetophenone in 65 ml of isopropanol was added a solution of 2.9 g of sodium hydroxide in 6 ml of water under a nitrogen atmosphere, and the mixture was stirred at 45° C. for 8 hours. After neutralization with dilute hydrochloric acid with ice cooling, the mixture was extracted with ethyl acetate. The organic layer was washed with water and dried, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography with n-hexane including 1% ethyl acetate. The resulting fractions containing the end compound was recrystallized from isopropanol to give 3.23 g of 2-n-heptyl-2'-hydroxy-4'-(3-methyl-2-butenyloxy)-chalcone as yellow needles.

Aufarbeitung

  1. extractionAfter neutralization with dilute hydrochloric acid with ice cooling, the mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. customdried
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography with n-hexane including 1% ethyl acetate
  6. additionThe resulting fractions containing the end compound
  7. customwas recrystallized from isopropanol

Quellen und Nachweise

ORD-Eintrag
ord-14c7f836cf2a448d944851c28c111bac
Quelldatensatz
uspto-grants-1992_02
Patentnummer
US05089654

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