3-Hydroxybenzaldehyde → 2-[2-(Diethylamino)ethoxy]benzaldehyde

Reaction equation

O[C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6].[CH2:10]([O-:12])[CH3:11].[Na+].Cl[CH2:15][CH2:16][N:17](CC)[CH2:18][CH3:19]>C(O)C>[CH2:16]([N:17]([CH2:11][CH2:10][O:12][C:7]1[CH:8]=[CH:9][CH:2]=[CH:3][C:4]=1[CH:5]=[O:6])[CH2:18][CH3:19])[CH3:15]

Participants

Procedure

6.1 g (50 mmol) of 3-hydroxybenzaldehyde were dissolved in 100 ml of ethanol and 3.5 g (50 mmol) of sodium ethanolate were added. The mixture was stirred for 15 minutes. Then 7.5 g (55 mmol) of N-(2-chloroethyl)-N,N-diethylamine were added, and the mixture was refluxed for 12 hours. The reaction mixture was then concentrated in vacuo. The residue was then partitioned between ether and 1M sodium hydroxide solution, and the ether phase was separated off, dried and concentrated in vacuo. 7.6 g of the intermediate were obtained.