Crystal structure of the monoglycidyl ether of isoeugenol
Résumé
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 \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.
Domaines
Cristallographie
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