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

İŞLEYEN A., Dogan O.

SYNTHESIS-STUTTGART, no.9, pp.1427-1432, 2006 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Publication Date: 2006
  • Doi Number: 10.1055/s-2006-926445
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.1427-1432
  • Middle East Technical University Affiliated: Yes


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.