Crystal structure of the monoglycidyl ether of isoeugenol

The title compound, C(13)H(16)O(3) [GE-isoEu; systematic name: 2-({2-meth­oxy-4-[(E)-1-propen-1-yl]phen­oxy}meth­yl)oxirane], which crystallizes in the triclinic P [Image: see text] 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.