Synthesis of Octahydro-2H-Chromen-4-ol from Vanillin and Isopulegol over Acid Modified Montmorillonite Clays: Effect of Acidity on the Prins Cyclization | Sciact - CRIS-system of Boreskov Institute of Catalysis

Synthesis of Octahydro-2H-Chromen-4-ol from Vanillin and Isopulegol over Acid Modified Montmorillonite Clays: Effect of Acidity on the Prins Cyclization Full article

Journal

Journal of Molecular Catalysis A: Chemical
ISSN: 1381-1169

Output data

Year: 2015, Volume: 398, Pages: 26-34 Pages count : 9 DOI: 10.1016/j.molcata.2014.11.016

Tags

(-)-Isopulegol Vanillin, Acid-activated montmorillonite, Octahydro-2H-chromen-4-ol, Prins cyclization reaction

Authors

Timofeeva Maria N. ^1,2,3 , Volcho Konstantin P. ^2,4 , Mikhalchenko Oksana S. ² , Panchenko Valentina N. ^1,2 , Krupskaya Victoria V. ^5,6 , Tsybulya Sergey V. ^1,2 , Gil Antonio ⁷ , Vicente Miguel A. ⁸ , Salakhutdinov Nariman F. ^2,4

Affiliations

1	Boreskov Institute of Catalysis SB RAS, Prospekt Akad. Lavrentieva 5, 630090 Novosibirsk, Russian Federation
2	Novosibirsk State University, Pirogova St. 2, 630090 Novosibirsk, Russian Federation
3	Novosibirsk State Technical University, Prospekt K. Marksa 20, 630092 Novosibirsk, Russian Federation
4	Novosibirsk Institute of Organic Chemistry SB RAS, Prospekt Akad. Lavrentieva 9, 630090 Novosibirsk, Russian Federation
5	Institute of Geology of Ore Deposits, Petrography, Mineralogy and Geochemistry RAS, Staromonetny Pr. 35, 119017 Moscow, Russian Federation
6	Moscow State University, Leninskie Gory 1, 119991 Moscow, Russian Federation
7	Department of Applied Chemistry, Public University of Navarra, 31006 Pamplona, Spain
8	Department of Inorganic Chemistry, University of Salamanca, Salamanca, Spain

Funding (6)

1	Federal Agency for Scientific Organizations	V.44.2.12.
2	Russian Foundation for Basic Research	14-03-00854
3	Russian Foundation for Basic Research	14-05-00297
4	Ministry of Economic Affairs and Digital Transformation	MAT2013-47811-C2-1-R, MAT2013-47811-C2-2-R
5	The Ministry of Education and Science of the Russian Federation
6	Ministry of Economic Affairs and Digital Transformation

Two calcium-rich natural layered aluminosilicates containing 90-95 wt.% montmorillonite were chemically activated using 0.125-3.0 M HCl solutions. Structural and textural properties were characterized by X-ray diffraction, elemental analysis and N2-adsorption/desorption analyses. According to infrared spectroscopy using pyridine as probe molecule, the amount of Brønsted acid sites increased when increasing HCl concentration. The catalytic performance of these materials was investigated in the Prins cyclization of (-)-isopulegol with vanillin to form octahydro-2H-chromen-4-ol, carried out in toluene at 35 ºC. It was found that the amount of Brønsted acid sites and the microporosity of the catalysts are key factors for the control of the reaction rate and the selectivity towards octahydro-2H-chromen-4-ol.

Timofeeva M.N. , Volcho K.P. , Mikhalchenko O.S. , Panchenko V.N. , Krupskaya V.V. , Tsybulya S.V. , Gil A. , Vicente M.A. , Salakhutdinov N.F.
Synthesis of Octahydro-2H-Chromen-4-ol from Vanillin and Isopulegol over Acid Modified Montmorillonite Clays: Effect of Acidity on the Prins Cyclization
Journal of Molecular Catalysis A: Chemical. 2015. V.398. P.26-34. DOI: 10.1016/j.molcata.2014.11.016 WOS Scopus РИНЦ ANCAN OpenAlex

Submitted:	Oct 9, 2014
Accepted:	Nov 17, 2014
Published online:	Nov 24, 2014
Published print:	Mar 1, 2015

Web of science:	WOS:000352115600004
Scopus:	2-s2.0-84919345048
Elibrary:	24019505
Chemical Abstracts:	2014:2012799
Chemical Abstracts (print):	162:160846
OpenAlex:	W2010932221

DB	Citing
Web of science	36
Scopus	37
Elibrary	34
OpenAlex	39