Boron trifluoride mediated Prins reaction of methylene diacetate with styrenes. One-pot synthesis of 3-chloro-3-arylpropanols

Date

2006-05-03

Author

İŞLEYEN, ALPER
Doğan, Özdemir

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A one-pot procedure was developed for the synthesis of 3-chloro-3-arylpropanols, which are important starting materials for the synthesis of biologically active benzanilide derivatives. Styrenes were reacted with methylene diacetate in the presence of boron trifluoride to give the corresponding 3-chloro-3-arylpropanols in 36-84% yield by the Prins reaction. A strongly electron-donating methoxy substituent at either the ortho or para position of the styrene did not give the expected 3-chloro-3-arylpropanols due to polymerization. Styrene with a strongly electron-withdrawing nitro substituent gave the corresponding 3-chloro-3-arylpropanol in very low yield. Under the same reaction conditions, substituted norbornene gave a tricyclic ether. A very easy procedure for the synthesis of methylene diacetate is also reported.

Subject Keywords

Organic Chemistry, Catalysis

URI

https://hdl.handle.net/11511/37397

Collections

Department of Chemistry, Article