Cargando…

Dimethyl 4,5-di­chloro­phthalate

While endeavoring to synthesize new chlorinated ligands for ruthenium-based metathesis catalysts, the title compound dimethyl 4,5-di­chloro­phthalate, C(10)H(8)Cl(2)O(4), was prepared from commercially available 4,5-di­chloro­phthalic acid in ∼77% yield. The title mol­ecule, which also finds utility...

Descripción completa

Detalles Bibliográficos
Autores principales: Hickstein, Daniel D., Reinheimer, Eric W., Johnson, Adam R., O’Leary, Daniel J.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2021
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9462297/
https://www.ncbi.nlm.nih.gov/pubmed/36340982
http://dx.doi.org/10.1107/S2414314621010439
_version_ 1784787153903943680
author Hickstein, Daniel D.
Reinheimer, Eric W.
Johnson, Adam R.
O’Leary, Daniel J.
author_facet Hickstein, Daniel D.
Reinheimer, Eric W.
Johnson, Adam R.
O’Leary, Daniel J.
author_sort Hickstein, Daniel D.
collection PubMed
description While endeavoring to synthesize new chlorinated ligands for ruthenium-based metathesis catalysts, the title compound dimethyl 4,5-di­chloro­phthalate, C(10)H(8)Cl(2)O(4), was prepared from commercially available 4,5-di­chloro­phthalic acid in ∼77% yield. The title mol­ecule, which also finds utility as a precursor mol­ecule 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 inter­actions 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 mol­ecules parallel to b. [Image: see text]
format Online
Article
Text
id pubmed-9462297
institution National Center for Biotechnology Information
language English
publishDate 2021
publisher International Union of Crystallography
record_format MEDLINE/PubMed
spelling pubmed-94622972022-11-04 Dimethyl 4,5-di­chloro­phthalate Hickstein, Daniel D. Reinheimer, Eric W. Johnson, Adam R. O’Leary, Daniel J. IUCrdata Data Reports While endeavoring to synthesize new chlorinated ligands for ruthenium-based metathesis catalysts, the title compound dimethyl 4,5-di­chloro­phthalate, C(10)H(8)Cl(2)O(4), was prepared from commercially available 4,5-di­chloro­phthalic acid in ∼77% yield. The title mol­ecule, which also finds utility as a precursor mol­ecule 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 inter­actions 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 mol­ecules parallel to b. [Image: see text] International Union of Crystallography 2021-10-13 /pmc/articles/PMC9462297/ /pubmed/36340982 http://dx.doi.org/10.1107/S2414314621010439 Text en © Hickstein et al. 2021 https://creativecommons.org/licenses/by/4.0/This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
spellingShingle Data Reports
Hickstein, Daniel D.
Reinheimer, Eric W.
Johnson, Adam R.
O’Leary, Daniel J.
Dimethyl 4,5-di­chloro­phthalate
title Dimethyl 4,5-di­chloro­phthalate
title_full Dimethyl 4,5-di­chloro­phthalate
title_fullStr Dimethyl 4,5-di­chloro­phthalate
title_full_unstemmed Dimethyl 4,5-di­chloro­phthalate
title_short Dimethyl 4,5-di­chloro­phthalate
title_sort dimethyl 4,5-di­chloro­phthalate
topic Data Reports
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9462297/
https://www.ncbi.nlm.nih.gov/pubmed/36340982
http://dx.doi.org/10.1107/S2414314621010439
work_keys_str_mv AT hicksteindanield dimethyl45dichlorophthalate
AT reinheimerericw dimethyl45dichlorophthalate
AT johnsonadamr dimethyl45dichlorophthalate
AT olearydanielj dimethyl45dichlorophthalate