Crystal structure of the monoglycidyl ether of isoeugenol

Abstract

The title compound, C₁₃H₁₆O₃ [GE-isoEu; systematic name: 2-({2-meth-oxy-4-[(E)-1-propen-1-yl]phen-oxy}meth-yl)oxirane], which crystallizes in the triclinic P space group, was synthesized in one step from iso-eugenol, a bio-based phenyl-propanoid, with an excess of epi-chloro-hydrin. Colourless prismatic crystals suitable for X-ray diffraction were obtained from a mixture of ethyl acetate and cyclo-hexane, 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-tris-ubstituted benzene ring by diglycidyl ether, meth-oxy and 1-(E)-propenyl groups, respectively. In the crystal, mol-ecules are organized through offset π-stacking inter-actions. Chemically, GE-isoEu constitutes an inter-mediate in the synthesis protocol of 2-[3-meth-oxy-4-(2-oxiranylmeth-oxy)phen-yl]-3-methyl-oxirane (GEEp-isoEu), a di-epoxy-dized monomer used in the manufacturing of thermosetting resins and intended for the elaboration of bio-composites.

Keywords: bio-based mol­ecule; crystal structure; isoeugenol deriv­ative; oxirane; phenyl­propene.