反応 #94013

反応方程式

3,4-dichloroaniline

cyclopentene oxide

→

trans-2-(3,4-dichloroanilino)cyclopentanol

収率 44.0%

反応条件

後処理

1. 1
   その他The solution is evaporated
2. 2
   その他the residue triturated with 250 ml
3. 3
   その他of petroleum ether (b.p. 30°-60° C.) five times to remove unreacted 3,4-dichloroaniline
4. 4
   workup.ADDITIONThe residue is treated with excess ethereal hydrogen chloride
5. 5
   その他the resulting crude hydrochloride salt is recrystallized twice from a methanol/ethyl ether mixture

実験手順

A solution of 50.0 g. (0.31 mole) of 3,4-dichloroaniline in 100 ml. of cyclopentene oxide is refluxed for 7 days. The solution is evaporated and the residue triturated with 250 ml. of petroleum ether (b.p. 30°-60° C.) five times to remove unreacted 3,4-dichloroaniline. The residue is treated with excess ethereal hydrogen chloride and the resulting crude hydrochloride salt is recrystallized twice from a methanol/ethyl ether mixture to give trans-2-(3,4-dichloroanilino)cyclopentanol, 38.7 g. (44% yield), m.p. 167°-168° C. The ultraviolet, infrared and nuclear magnetic resonance spectra are consistent with the structure of this product.

出典