Crystal structure of the monoglycidyl ether of isoeugenol

Abstract

The title compound, C13H16O3 [GE-isoEu; systematic name: 2-({2-methoxy-4-[(E)-1-propen-1-yl]phenoxy}methyl)oxirane], which crystallizes in the triclinic P\overline{1} space group, was synthesized in one step from iso-eugenol, a bio-based phenylpropanoid, with an excess of epichlorohydrin. Colourless prismatic crystals suitable for X-ray diffraction were obtained from a mixture of ethyl acetate and cyclohexane, during purification by column chromatography on silica gel. GE-isoEu, which corresponds to the trans isomer of the monoglycidyl ether of iso-eugenol, is based on a 1,2,4-trisubstituted benzene ring by diglycidyl ether, methoxy and 1-(E)-propenyl groups, respectively. In the crystal, molecules are organized through offset π-stacking interactions. Chemically, GE-isoEu constitutes an intermediate in the synthesis protocol of 2-[3-methoxy-4-(2-oxiranylmethoxy)phenyl]-3-methyloxirane (GEEp-isoEu), a diepoxydized monomer used in the manufacturing of thermosetting resins and intended for the elaboration of bio-composites.