Abstract
While endeavoring to synthesize new chlorinated ligands for ruthenium-based metathesis catalysts, the title compound dimethyl 4,5-di-chloro-phthalate, C10H8Cl2O4, was prepared from commercially available 4,5-di-chloro-phthalic acid in ∼77% yield. The title mol-ecule, which also finds utility as a precursor mol-ecule for the synthesis of drugs used in the treatment of Alzheimer's disease, shows one carbonyl-containing methyl ester moiety lying nearly co-planar with the chlorine-derivatized aromatic ring while the second methyl ester shows a significant deviation of 101.05 (12)° from the least-squares plane of the aromatic ring. Within the crystal, structural integrity is maintained by the concerted effects of electrostatic inter-actions involving the electron-deficient carbonyl carbon atom and the electron-rich aromatic ring along the a-axis direction and C-H⋯O hydrogen bonds between neighboring mol-ecules parallel to b.
Highlights
While endeavoring to synthesize new chlorinated ligands for ruthenium-based metathesis catalysts, the title compound dimethyl 4,5-dichlorophthalate, C10H8Cl2O4, was prepared from commercially available 4,5-dichlorophthalic acid in $77% yield
Structural integrity is maintained by the concerted effects of electrostatic interactions involving the electron-deficient carbonyl carbon atom and the electron-rich aromatic ring along the a-axis direction and C—HÁ Á ÁO hydrogen bonds between neighboring molecules parallel to b
Looking down the a-axis, and involving a second molecule of 1 related by inversion, the centroid of the electron-rich, chlorine-derivatized aromatic ring of the first molecule lies above the electron-deficient carbonyl carbon atom of the second at a distance of 3.4600 (12) A, suggesting the presence of electrostatic interactions (Fig. 2)
Summary
While endeavoring to synthesize new chlorinated ligands for ruthenium-based metathesis catalysts (Anderson et al, 2006), the title compound, 1, was prepared from commercially available 4,5-dichlorophthalic acid in $77% yield. The title molecule finds utility as a precursor molecule for the synthesis of drugs used in the treatment of Alzheimer’s disease (Hennessy & Buchwald, 2005). Compound 1 crystallizes in the centrosymmetric triclinic space group P1 with a full molecule of the title compound as the contents of asymmetric unit (Fig. 1, Table 1). Within the structure of 1, one of the carbonyl-containing ester groups is nearly co-planar with the aromatic ring demonstrating a deviation of 3.41 (12) from the least-squares plane of the chlorine-derivatized aromatic ring.
Sign-in/Register to view highlights & summary Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a callDisclaimer: All third-party content on this website/platform is and will remain the property of their respective owners and is provided on "as is" basis without any warranties, express or implied. Use of third-party content does not indicate any affiliation, sponsorship with or endorsement by them. Any references to third-party content is to identify the corresponding services and shall be considered fair use under The CopyrightLaw.
