PRINS CYCLIZATION OF ISOVALERALDEHYDE AND ISOPRENOL

Kód výsledku v IS VaVaI

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Výsledek na webu

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DOI - Digital Object Identifier

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Jazyk výsledku

angličtina

Název v původním jazyce

PRINS CYCLIZATION OF ISOVALERALDEHYDE AND ISOPRENOL

Popis výsledku v původním jazyce

2-iso-Butyl-4-methyl-tetrahydro-2H-pyran-4-ol, also called Florosa or Florol, is commercially very attractive compound due to its fragrant properties. It is usually prepared by acid catalyzed Prins cyclization of isovaleraldehyde and isoprenol. The mechanism of Prins cyclization consists of, in the first step, the formation of hemiacetal (reaction of one molecule of aldehyde and alcohol), followed by cyclization of hemiacetal to cyclic carbocationic intermediate. Carbocationic intermediate is attacked by nucleophile from reaction media or catalyst, forming the product - tetrahydropyran-4-ol or undesired dihydropyranes. Separation of these products from reaction mixture is a very complicated process, so the leading of the reaction with very high selectivity is a crucial step in the reaction. In this work the different catalytic systems were tested for Prins cyclization - Bronsted and Lewis acid catalysts (both types in heterogeneous and homogeneous forms) and also the reaction condition

Název v anglickém jazyce

PRINS CYCLIZATION OF ISOVALERALDEHYDE AND ISOPRENOL

Popis výsledku anglicky

2-iso-Butyl-4-methyl-tetrahydro-2H-pyran-4-ol, also called Florosa or Florol, is commercially very attractive compound due to its fragrant properties. It is usually prepared by acid catalyzed Prins cyclization of isovaleraldehyde and isoprenol. The mechanism of Prins cyclization consists of, in the first step, the formation of hemiacetal (reaction of one molecule of aldehyde and alcohol), followed by cyclization of hemiacetal to cyclic carbocationic intermediate. Carbocationic intermediate is attacked by nucleophile from reaction media or catalyst, forming the product - tetrahydropyran-4-ol or undesired dihydropyranes. Separation of these products from reaction mixture is a very complicated process, so the leading of the reaction with very high selectivity is a crucial step in the reaction. In this work the different catalytic systems were tested for Prins cyclization - Bronsted and Lewis acid catalysts (both types in heterogeneous and homogeneous forms) and also the reaction condition

Druh

D - Stať ve sborníku

CEP obor

CC - Organická chemie

OECD FORD obor

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Projekt

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Návaznosti

I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Rok uplatnění

2015

Kód důvěrnosti údajů

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

Název statě ve sborníku

Proceedings of the 3rd International Conference on Chemical Technology

ISBN

978-80-86238-79-1

ISSN

2336-811X

e-ISSN

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Počet stran výsledku

4

Strana od-do

27-30

Název nakladatele

Česká společnost průmyslové chemie (ČSPCH)

Místo vydání

Praha

Místo konání akce

Mikulov

Datum konání akce

13. 4. 2015

Typ akce podle státní příslušnosti

WRD - Celosvětová akce

Kód UT WoS článku

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