A synthetic route to 4-alkyl-?-methylhydrocinnamylaldehydes
The result's identifiers
Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F60461373%3A22310%2F17%3A43913218" target="_blank" >RIV/60461373:22310/17:43913218 - isvavai.cz</a>
Result on the web
<a href="http://dx.doi.org/10.1007/s11164-016-2782-6" target="_blank" >http://dx.doi.org/10.1007/s11164-016-2782-6</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1007/s11164-016-2782-6" target="_blank" >10.1007/s11164-016-2782-6</a>
Alternative languages
Result language
angličtina
Original language name
A synthetic route to 4-alkyl-?-methylhydrocinnamylaldehydes
Original language description
The 4-Alkyl-a-methylhydrocinnamylaldehydes (alkyl-isopropyl, isobutyl, methyl) are frequently used fragrances with desired floral (lilac, cyclamen, lily-of-the-valley) scent. These substances are valued for their good stability in basic solution and, therefore, are frequently used in soaps, detergents, or shampoos. These substances are synthesized by a two-step synthesis involving base catalyzed aldol condensation of 4-alkylbenzaldehyde with propanal followed by selective hydrogenation of the C=C bond. In aldol condensation, selectivity is decreased by formation of undesired products of propanal autocondensation 2-methylpent-2-enal. In this work the reaction conditions for homogenous catalyzed aldol condensation of 4-isobutylbenzadehyde with propanal were tested (catalyst type and amount, molar ratio of reactants, solvent type). Reaction conditions giving the best results (92% conversion, 79% selectivity) were adapted to other 4-alkyl-a-methylcinnamylaldehydes preparation with similar results. In the second step?hydrogenation of aldol product different types of catalyst (nickel, cobalt, palladium or Adkins catalyst), and also different solvents, were tested. Hydrogenation conditions leading to the highest yield (72% selectivity at 95% conversion) were adapted to other 4-alkylhydrocinnamyladehydes with similar results.
Czech name
—
Czech description
—
Classification
Type
J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database
CEP classification
—
OECD FORD branch
10401 - Organic chemistry
Result continuities
Project
—
Continuities
S - Specificky vyzkum na vysokych skolach
Others
Publication year
2017
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
Research on Chemical Intermediates
ISSN
0922-6168
e-ISSN
—
Volume of the periodical
43
Issue of the periodical within the volume
neuveden
Country of publishing house
NL - THE KINGDOM OF THE NETHERLANDS
Number of pages
11
Pages from-to
2603-2613
UT code for WoS article
000398183900039
EID of the result in the Scopus database
—