Synthesis of aryl-butanal isomers by hydroformylation of substituted allylbenzene and propenylbenzene

László Kollár, Edit Farkas, Joan Bâtiu

Research output: Contribution to journalArticle

36 Citations (Scopus)

Abstract

The hydroformylation of two isomeric arylalkenes, 1-(4'-methoxy-phenyl)- propene and 3-(4'-methoxy-phenyl)-propene was investigated in the presence of in situ rhodium and platinum catalysts. While α- and β-substituted formyl regioisomers were formed in the hydroformylation of propenylarene type substrate by rhodium catalysts, all three regioisomers were isolated in platinum-catalyzed reactions. Very high chemoselectivities (> 99%) were obtained in the first case. The accompanying hydrogenation of the substrate took place to a very small extent. Due to isomerization of the terminal double bond lower chemoselectivities and the formation of chiral 2-(4'- methoxy)-butanal were observed with 3-(4'-methoxyphenyl)-propene as substrate. E.e.'s up to 7.5% and 27.5% were obtained for 2-(4'-methoxy)- butanal in asymmetric hydroformylation of 1-(4'-methoxy-phenyl)-propene by rhodium-diop catalyst and in the hydroformylation of 3-(4'-methoxy-phenyl)- propene by platinum-tin(II)chloride catalyst, respectively.

Original languageEnglish
Pages (from-to)283-288
Number of pages6
JournalJournal of Molecular Catalysis A: Chemical
Volume115
Issue number2
DOIs
Publication statusPublished - Jan 29 1997

Keywords

  • Anethol
  • Estragol
  • Hydroformylation
  • Platinum- phosphine-tin(II)chloride catalyst
  • Rhodium-phosphine catalyst

ASJC Scopus subject areas

  • Catalysis
  • Process Chemistry and Technology
  • Physical and Theoretical Chemistry

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