Reaction of 2(10)-Pinene with CAN(MeOH)/SiO2 [Cerium (IV) Ammonium Nitrate and Methanol Adsorbed on Silica Gel] Reagent

Abstract

The reaction of 2(10)-pinene (1) with cerium (IV) ammonium nitrate (CAN) and methanol adsorbed on silica gel [CAN(MeOH)/SiO₂] reagent was studied in order to synthesize methyl α-terpinyl ether (4).
The CAN(MeOH)/SiO₂ reagent was easily prepared by the addition of a weighed amount of silica gel to a solution of CAN in methanol and the methanol was removed by 82% under reduced pressure.
CAN(MeOH)/SiO₂ was found to be an effective reagent for the etherification of (1).
(4) was obtained as the major product from (1) in an isolated yield of 58%.
(4) was also obtained from 2-pinene and d-limonene.
α-Terpineol was obtained by reaction of (1) with the CAN(H₂O)/SiO₂ reagent.