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

Beteiligte Stoffe

Reaktionsschritte

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.

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