High-yielding preparation of fragrance Clarycet via two-step synthesis

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F60461373%3A22310%2F23%3A43928208" target="_blank" >RIV/60461373:22310/23:43928208 - isvavai.cz</a>

Výsledek na webu

<a href="https://link.springer.com/article/10.1007/s11164-022-04882-8" target="_blank" >https://link.springer.com/article/10.1007/s11164-022-04882-8</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1007/s11164-022-04882-8" target="_blank" >10.1007/s11164-022-04882-8</a>

Jazyk výsledku

angličtina

Název v původním jazyce

High-yielding preparation of fragrance Clarycet via two-step synthesis

Popis výsledku v původním jazyce

Clarycet (4-methyl-2-propyltetrahydro-2H-pyran-4-yl acetate) is an important fragrance used in many industrial applications ranging from cosmetics to agrochemical products. There are several procedures for its preparation, while two-step synthesis consisting of Prins cyclization followed by esterification appears to be simpler and higher yielding comparing to other procedures. Therefore, we sought for the optimal reaction conditions of both steps. We found that the highest yields of the desired substituted tetrahydropyranol (THPol) in Prins cyclization of butanal with isoprenol can be achieved under the following conditions: 70 degrees C, catalyst 1 mol% 10% sulphuric acid, 250 mol% of water, no solvent (butanal conversion 93%, selectivity to THPol 82% after 5 h of reaction). The second reaction step, esterification of THPol with acetic anhydride, was optimized yielding 98% of Clarycet under the following reaction conditions: molar ratio THPol:acetic anhydride 1:5, catalyst 1 mol% FeCl3, room temperature, no solvent, 5 min of reaction. The availability of the catalysts used, the possibility of performing the reactions without the addition of the solvent, and the high yields of the product showed good potential of this arrangement for Clarycet preparation.

Název v anglickém jazyce

High-yielding preparation of fragrance Clarycet via two-step synthesis

Popis výsledku anglicky

Clarycet (4-methyl-2-propyltetrahydro-2H-pyran-4-yl acetate) is an important fragrance used in many industrial applications ranging from cosmetics to agrochemical products. There are several procedures for its preparation, while two-step synthesis consisting of Prins cyclization followed by esterification appears to be simpler and higher yielding comparing to other procedures. Therefore, we sought for the optimal reaction conditions of both steps. We found that the highest yields of the desired substituted tetrahydropyranol (THPol) in Prins cyclization of butanal with isoprenol can be achieved under the following conditions: 70 degrees C, catalyst 1 mol% 10% sulphuric acid, 250 mol% of water, no solvent (butanal conversion 93%, selectivity to THPol 82% after 5 h of reaction). The second reaction step, esterification of THPol with acetic anhydride, was optimized yielding 98% of Clarycet under the following reaction conditions: molar ratio THPol:acetic anhydride 1:5, catalyst 1 mol% FeCl3, room temperature, no solvent, 5 min of reaction. The availability of the catalysts used, the possibility of performing the reactions without the addition of the solvent, and the high yields of the product showed good potential of this arrangement for Clarycet preparation.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

—

OECD FORD obor

10401 - Organic chemistry

Projekt

—

Návaznosti

S - Specificky vyzkum na vysokych skolach

Rok uplatnění

2023

Kód důvěrnosti údajů

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

Název periodika

RESEARCH ON CHEMICAL INTERMEDIATES

ISSN

0922-6168

e-ISSN

1568-5675

Svazek periodika

49

Číslo periodika v rámci svazku

2

Stát vydavatele periodika

UZ - Republika Uzbekistán

Počet stran výsledku

11

Strana od-do

577-587

Kód UT WoS článku

000889027400002

EID výsledku v databázi Scopus

2-s2.0-85142676929