反应详情

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.

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