4-Hydroxybenzaldehyde → 4-[[6-(Diethylamino)hexyl]oxy]benzaldehyde

HRID 1030668

Reaktionsgleichung

Reaktionsgleichung von HRID 1030668
[CH2:1]([N:3]([CH2:11][CH3:12])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][OH:10])[CH3:2].O[C:14]1[CH:21]=[CH:20][C:17]([CH:18]=[O:19])=[CH:16][CH:15]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[CH2:11]([N:3]([CH2:1][CH3:2])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][O:10][C:14]1[CH:21]=[CH:20][C:17]([CH:18]=[O:19])=[CH:16][CH:15]=1)[CH3:12]

Komponenten

6

Edukt 4

HCID 1264-HydroxybenzaldehydeHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 2450546-(Diethylamino)-1-hexanol

Produkt 1

HCID 197610134-[[6-(Diethylamino)hexyl]oxy]benzaldehydeAusbeute 64,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A mixture of 2.17 g of 6-diethylamino-1-hexanol (J. Chem. Soc. 1942, 428), 1.52 g of 4-hydroxy-benzaldehyde and 3.3 g of triphenylphosphine in 100 ml of tetrahydrofuran was treated slowly at 20° with a solution of 1.97 g of diethyl azodicarboxylate. After the dropwise addition the mixture was stirred at room temperature for a further 5 hours. The reaction mixture was then evaporated in a rotary evaporator. The residue was chromatographed on 400 g of neutral aluminium oxide (activity grade III) with hexane:ethyl acetate 7:3). There were obtained 2.22 g (64%) of 4- [[6-(diethylamino)hexyl]oxy]benzaldehyde as a yellowish oil.

Aufarbeitung

  1. additionAfter the dropwise addition the mixture
  2. customThe reaction mixture was then evaporated in a rotary evaporator
  3. customThe residue was chromatographed on 400 g of neutral aluminium oxide (activity grade III) with hexane:ethyl acetate 7:3)

Quellen und Nachweise

ORD-Eintrag
ord-f1eabd7553d241a58f3f3f205ce4c971
Quelldatensatz
uspto-grants-1992_04
Patentnummer
US05106878

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