Highly selective non-catalytic Claisen rearrangement in a high-pressure and high-temperature water microreaction system
2011
Abstract High-pressure and high-temperature water (HPHT-H 2 O) microreaction system was proven to be an efficient method to carry out the non-catalytic Claisen rearrangement. Allyl phenyl ether undergoes Claisen rearrangement to obtain o -allylphenol with a very high yield and selectivity of 98% within a short reaction time of 13.4 s at 265 °C and 5 MPa pressure. Compare to the solvent-free microreaction, HPHT-H 2 O plays an important role to accelerate the reaction as a catalyst by transferring a proton along locally formed hydrogen bond with the substrate. Finally, the obtained product can be separated completely from the aqueous suspension within the time range of 40 min to 24 h after the reaction. Even though the reaction has occurred in aqueous conditions, little side reactions, such as hydrolysis, hydration, or pyrolysis, was found.
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