Prins cyclization in 4-methyl-2-phenyl-tetrahydro-2H-pyran-4-ol preparation using smectite clay as catalyst

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61388955%3A_____%2F18%3A00506548" target="_blank" >RIV/61388955:_____/18:00506548 - isvavai.cz</a>

Výsledek na webu

<a href="http://hdl.handle.net/11104/0297780" target="_blank" >http://hdl.handle.net/11104/0297780</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1007/s11144-018-1371-7" target="_blank" >10.1007/s11144-018-1371-7</a>

Jazyk výsledku

angličtina

Název v původním jazyce

Prins cyclization in 4-methyl-2-phenyl-tetrahydro-2H-pyran-4-ol preparation using smectite clay as catalyst

Popis výsledku v původním jazyce

Prins cyclization of isoprenol with benzaldehyde as a model aldehyde was performed using montmorillonite K10 as an acid catalyst. Various reaction conditions were used including catalyst modification by mineral acids and calcination. Both treatments influenced the selectivity to substituted tetrahydropyranol negatively. Due to the increased specific surface of the catalyst the reaction rate increased. Both addition of water and methanol to the reaction mixture prevented dehydration but the selectivity to desired product remained the same. Chosen reaction conditions (70 A degrees C, ratio aldehyde:isoprenol 0.9:1, catalyst amount 110 wt%, solvent toluene) were used in Prins cyclization of other aldehydes with the similar results. Montmorillonite K10 may be used in preparation of substituted tetrahydropyranols with selectivity ranging from 59 to 69% (depending on aldehyde), which is comparable with or higher than heterogeneous catalysts used previously. This catalyst may be also used repeatedly with slight decrease in the reaction rate and no loss of selectivity.

Název v anglickém jazyce

Prins cyclization in 4-methyl-2-phenyl-tetrahydro-2H-pyran-4-ol preparation using smectite clay as catalyst

Popis výsledku anglicky

Prins cyclization of isoprenol with benzaldehyde as a model aldehyde was performed using montmorillonite K10 as an acid catalyst. Various reaction conditions were used including catalyst modification by mineral acids and calcination. Both treatments influenced the selectivity to substituted tetrahydropyranol negatively. Due to the increased specific surface of the catalyst the reaction rate increased. Both addition of water and methanol to the reaction mixture prevented dehydration but the selectivity to desired product remained the same. Chosen reaction conditions (70 A degrees C, ratio aldehyde:isoprenol 0.9:1, catalyst amount 110 wt%, solvent toluene) were used in Prins cyclization of other aldehydes with the similar results. Montmorillonite K10 may be used in preparation of substituted tetrahydropyranols with selectivity ranging from 59 to 69% (depending on aldehyde), which is comparable with or higher than heterogeneous catalysts used previously. This catalyst may be also used repeatedly with slight decrease in the reaction rate and no loss of selectivity.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

—

OECD FORD obor

10403 - Physical chemistry

Projekt

—

Návaznosti

I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Rok uplatnění

2018

Kód důvěrnosti údajů

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Název periodika

Reaction Kinetics Mechanism and Catalysis

ISSN

1878-5190

e-ISSN

—

Svazek periodika

124

Číslo periodika v rámci svazku

2

Stát vydavatele periodika

NL - Nizozemsko

Počet stran výsledku

15

Strana od-do

711-725

Kód UT WoS článku

000438687600017

EID výsledku v databázi Scopus

2-s2.0-85042109857