NDLI: Thermo-analytical determination of intermediates in the copper catalysed rearrangement of o-toluic acid to meta-cresol

Please wait, while we are loading the content...

Thermo-analytical determination of intermediates in the copper catalysed rearrangement of o-toluic acid to meta-cresol

Content Provider	Semantic Scholar
Author	Sunil, Abraham C. Langner, Ernst H. G. Marais, Charlene Bezuidenhoudt, Barend C. B.
Copyright Year	2013
Abstract	The intermediates formed during the conversion of o-toluic acid 2 to m-cresol 1 in the presence of Cu(II) according to the Keading process, together with the temperatures at which crucial changes occur, have been investigated by means of X-ray diffractometry [which confirmed the formation of the paddlewheel copper complex tetrakis(μ2-2-methylbenzoato)bis(2-methylbenzoic acid)copper(II) 5 with two apical o-toluic acid ligands], differential scanning calorimetry (DSC), thermogravimetric analysis (TGA), NMR spectroscopy, infrared spectrometry (IR) and Maldi-Tof mass spectrometry. The major chemical change observed at 164 °C might be ascribed to the dissociation of the apical o-toluic acid ligands from 5 to give tetrakis(μ2-2-methylbenzoato)copper(II) 6 accompanied by water loss. O–C bond formation between the carboxylate oxygens and ortho-carbons of the toluic acid moieties in adjacent paddlewheels of the stepped polymeric 6 is proposed to explain the formation of copper(I) 2-methyl-6-{[(2-methylphenyl)carbonyl]oxy}benzoate 8via intermediate 7 and initiates the decomposition observed by DSC at 236 °C. Decarboxylation of 8 at 249.5 °C gives 3-methylphenyl 2-methylbenzoate 4, which can be hydrolysed to o-toluic acid 2 and the target compound, m-cresol 1.
Starting Page	2227
Ending Page	2233
Page Count	7
File Format	PDF HTM / HTML
DOI	10.1039/C3CY00119A
Volume Number	3
Alternate Webpage(s)	http://www.rsc.org/suppdata/cy/c3/c3cy00119a/c3cy00119a.pdf
Alternate Webpage(s)	https://doi.org/10.1039/C3CY00119A
Language	English
Access Restriction	Open
Content Type	Text
Resource Type	Article

Central Library (ISO-9001:2015 Certified)
Indian Institute of Technology Kharagpur
Kharagpur, West Bengal, India | PIN - 721302

See location in the Map
03222 282435
Mail: support@ndl.gov.in

Sl.	Authority	Responsibilities	Communication Details
1	Ministry of Education (GoI), Department of Higher Education	Sanctioning Authority	https://www.education.gov.in/ict-initiatives
2	Indian Institute of Technology Kharagpur	Host Institute of the Project: The host institute of the project is responsible for providing infrastructure support and hosting the project	https://www.iitkgp.ac.in
3	National Digital Library of India Office, Indian Institute of Technology Kharagpur	The administrative and infrastructural headquarters of the project	Dr. B. Sutradhar bsutra@ndl.gov.in
4	Project PI / Joint PI	Principal Investigator and Joint Principal Investigators of the project	Dr. B. Sutradhar bsutra@ndl.gov.in Prof. Saswat Chakrabarti will be added soon
5	Website/Portal (Helpdesk)	Queries regarding NDLI and its services	support@ndl.gov.in
6	Contents and Copyright Issues	Queries related to content curation and copyright issues	content@ndl.gov.in
7	National Digital Library of India Club (NDLI Club)	Queries related to NDLI Club formation, support, user awareness program, seminar/symposium, collaboration, social media, promotion, and outreach	clubsupport@ndl.gov.in
8	Digital Preservation Centre (DPC)	Assistance with digitizing and archiving copyright-free printed books	dpc@ndl.gov.in
9	IDR Setup or Support	Queries related to establishment and support of Institutional Digital Repository (IDR) and IDR workshops	idr@ndl.gov.in