One-pot synthesis of diisobornyl ether from camphene using heteropoly acid catalysts

A novel one-pot catalytic synthesis of diisobornyl ether directly from camphene (1) has been developed. The reaction occurs under near ambient conditions in the presence of dissolved or silica-supported heteropoly acid H3PW12O40 (PW) as a catalyst to give diisobornyl ether (2) with up to 90% selectivity at 50–60% conversion, along with isoborneol (3). Ether 2 appears to be a new compound; it was isolated as a mixture of meso and dl stereoisomers and fully characterized by MS-GC, NMR and IR spectroscopy. The supported PW catalyst can be easily separated and reused; no PW leaching from support was observed during the reaction. Conventional acid catalysts such as H2SO4 or Amberlyst-15 showed no activity in this reaction.

Graphical abstractA novel one-pot catalytic synthesis of diisobornyl ether directly from camphene (1) has been developed. The reaction occurs under near ambient conditions in the presence of dissolved or silica-supported heteropoly acid H3PW12O40 (PW) as a catalyst to give diisobornyl ether (2) with up to 90% selectivity at 50–60% conversion. Figure optionsDownload full-size imageDownload as PowerPoint slide