Synthesis of E-3-Hydroxymethyl-1-methoxy-4-(1′-pentenyl)benzene

Abstract

The title compound with exclusively the E-geometry has been synthesized by two independent routes. When this compound was reacted with cerium (IV) ammonium nitrate, it was found that oxidative cyclisation to the corresponding 4-hydroxybenzo-pyrans did not occur. This further defines the structural parameters required for such oxidative cyclisations.