Design and synthesis of (E)-1-((3-ethyl-2,4,4-trimethylcyclohex-2-enylidene)methyl-4-substituted benzenes from 1-(2,6,6-trimethylcyclohex-1-enyl)ethanol

Chem Commun (Camb). 2009 Apr 28:(16):2133-5. doi: 10.1039/b823063c. Epub 2009 Mar 9.

Abstract

A novel strategy for synthesizing (E)-1-((3-ethyl-2,4,4-trimethylcyclohex-2-enylidene)methyl-4-substituted benzenes from 1-(2,6,6-trimethylcyclohex-1-enyl)ethanol has been developed; the allylic alcohol was treated with PPh(3).HBr in methanol followed by aldehydes in the presence of a base and furnished the 1,3-dienes in moderate to good yields (79-86%).

MeSH terms

  • Benzene Derivatives / chemical synthesis*
  • Benzene Derivatives / chemistry*
  • Cyclohexenes / chemistry*
  • Magnetic Resonance Spectroscopy
  • Mass Spectrometry

Substances

  • 1-(2,6,6-trimethylcyclohex-1-enyl)ethanol
  • Benzene Derivatives
  • Cyclohexenes