反应详情

A solution of 5-chloro-2-hydroxybenzaldehyde (25.68 g) in dry DMF (100 ml) was added dropwise to a stirred suspension of sodium hydride (6.84 g of a 60% dispersion in mineral oil) in dry DMF (100 ml) at ambient temperature under nitrogen with stirring. The mixture was heated on a steam bath for 1.5 hours, then cooled to ambient temperature and a solution of N-benzyl-2-chloro-N-methylethylamine in toluene (60 ml) [prepared by dissolving the hydrochloride (48.5 g) in 2M sodium hydroxide solution (50 ml) and extracting with toluene (2×30 ml) with drying] and the resulting mixture was heated on a steam bath for 4 hours. The mixture was cooled to ambient temperature and then poured into ice/water (100 ml). The mixture was extracted with ether and the combined ether extracts were washed with 2M sodium hydroxide solution until the washes were colourless. The ether extracts were then washed with 2M hydrochloric acid. The acidic extracts were basified with concentrated sodium hydroxide solution and extracted with dichloromethane to give an oil. A portion of the oil was dissolved in ether and treated with ethereal hydrogen chloride. The solid which precipitated was collected by filtration and recrystallised from propan-2-ol to give 2-[2-(N-benzyl-N-methylamino)ethoxy]-5-chlorobenzaldehyde, m.p. 154°-155° C.

1. temperatureThe mixture was heated on a steam bath for 1.5 hours
2. extractionextracting with toluene (2×30 ml)
3. customwith drying] and the resulting mixture
4. temperaturewas heated on a steam bath for 4 hours
5. temperatureThe mixture was cooled to ambient temperature
6. additionpoured into ice/water (100 ml)
7. extractionThe mixture was extracted with ether
8. washthe combined ether extracts were washed with 2M sodium hydroxide solution until the washes
9. washThe ether extracts were then washed with 2M hydrochloric acid
10. extractionextracted with dichloromethane
11. customto give an oil
12. customThe solid which precipitated
13. filtrationwas collected by filtration
14. customrecrystallised from propan-2-ol