反応 #352093

反応方程式

4-benzyloxy-3-hydroxy-benzaldehyde

NaH

3-methoxybromopropane

→

title compound

4-Benzyloxy-3-(3-methoxypropyloxy)-benzaldehyde

溶媒

dimethyl-formamide

dimethylformamide

dimethylformamide

反応条件

後処理

1. 1
   workup.STIRRINGthe mixture is stirred at room temperature for a further 4 hours
2. 2
   濃縮is then concentrated by evaporation under reduced pressure
3. 3
   その他The residue is partitioned between diethyl ether and water
4. 4
   乾燥The combined organic phases are dried over sodium sulfate
5. 5
   濃縮concentrated by evaporation
6. 6
   その他the residue is purified by FC (100 g of silica gel, dichloromethane)

実験手順

A solution of 28.8 g of 4-benzyloxy-3-hydroxy-benzaldehyde in 100 ml of dimethyl-formamide is added dropwise to a suspension of 5.54 g of NaH (60% dispersion in mineral oil) in 150 ml of absolute dimethylformamide. The reaction mixture is stirred at room temperature. After 30 minutes, a solution of 29 g of 3-methoxybromopropane in 120 ml of dimethylformamide is added thereto, and the mixture is stirred at room temperature for a further 4 hours and is then concentrated by evaporation under reduced pressure. The residue is partitioned between diethyl ether and water. The combined organic phases are dried over sodium sulfate and concentrated by evaporation, and the residue is purified by FC (100 g of silica gel, dichloromethane), yielding the title compound, which crystallises spontaneously: Rf (dichloromethane/diethyl ether)=0.44.

出典