Crystal structure of the monoglycidyl ether of isoeugenol.

The title compound, C 13 H 16 O 3 [ 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.