An improved method for aldol condensation catalyses by Amberlyst A-26 OH

Application in the synthesis of pseudoionone derivative, 11,15-dimethylhexadeca-8,10,14-trien-7-one

Daniel J W Chong, Florence H L Chong, Jalifah Latip

Research output: Contribution to journalArticle

1 Citation (Scopus)

Abstract

This paper reports the improved procedure for aldol condensation between citral and 2-octanone with Amberlyst A-26 OH to give 11,15-dimethyl-hexadeca-8,10,14-trien-7-one. The improved synthesis utilizing Amberlyst A-26 OH as the solid catalyst produces better yield (93.0%) and enables simple work-up procedure. The experimental conditions are evaluated and optimized at 2-octanone/citral molar ratio of 10, catalyst amount of 5% (mole of citral), and temperature of 60°C in 3.5 h reaction time. 11,15-Dimethyl-hexadeca-8,10,14-trien-7-one is isolated using preparative thin layer chromatography with hexane:ethyl acetate (9.5:0.5) and confirmed by gas chromatography-mass spectrometry (GC-MS), ultraviolet-visible (UV-Vis), Fourier transform infrared (FTIR) and nuclear magnetic resonance (NMR).

Original languageEnglish
Pages (from-to)297-304
Number of pages8
JournalGreen Processing and Synthesis
Volume5
Issue number3
DOIs
Publication statusPublished - 1 Jun 2016

Fingerprint

citral
Trientine
faropenem medoxomil
condensation
Condensation
catalyst
Derivatives
Thin layer chromatography
Catalysts
Hexane
Gas chromatography
Fourier transform
chromatography
Mass spectrometry
nuclear magnetic resonance
acetate
gas chromatography
Fourier transforms
mass spectrometry
Nuclear magnetic resonance

Keywords

  • 2-octanone
  • aldol condensation
  • Amberlyst A-26 OH
  • citral
  • pseudoionone

ASJC Scopus subject areas

  • Chemical Engineering(all)
  • Renewable Energy, Sustainability and the Environment
  • Fuel Technology
  • Environmental Chemistry
  • Health, Toxicology and Mutagenesis
  • Industrial and Manufacturing Engineering

Cite this

@article{2b7be19d0877402ab01608d234b1ed37,
title = "An improved method for aldol condensation catalyses by Amberlyst A-26 OH: Application in the synthesis of pseudoionone derivative, 11,15-dimethylhexadeca-8,10,14-trien-7-one",
abstract = "This paper reports the improved procedure for aldol condensation between citral and 2-octanone with Amberlyst A-26 OH to give 11,15-dimethyl-hexadeca-8,10,14-trien-7-one. The improved synthesis utilizing Amberlyst A-26 OH as the solid catalyst produces better yield (93.0{\%}) and enables simple work-up procedure. The experimental conditions are evaluated and optimized at 2-octanone/citral molar ratio of 10, catalyst amount of 5{\%} (mole of citral), and temperature of 60°C in 3.5 h reaction time. 11,15-Dimethyl-hexadeca-8,10,14-trien-7-one is isolated using preparative thin layer chromatography with hexane:ethyl acetate (9.5:0.5) and confirmed by gas chromatography-mass spectrometry (GC-MS), ultraviolet-visible (UV-Vis), Fourier transform infrared (FTIR) and nuclear magnetic resonance (NMR).",
keywords = "2-octanone, aldol condensation, Amberlyst A-26 OH, citral, pseudoionone",
author = "Chong, {Daniel J W} and Chong, {Florence H L} and Jalifah Latip",
year = "2016",
month = "6",
day = "1",
doi = "10.1515/gps-2015-0126",
language = "English",
volume = "5",
pages = "297--304",
journal = "Green Processing and Synthesis",
issn = "2191-9542",
publisher = "Walter de Gruyter GmbH",
number = "3",

}

TY - JOUR

T1 - An improved method for aldol condensation catalyses by Amberlyst A-26 OH

T2 - Application in the synthesis of pseudoionone derivative, 11,15-dimethylhexadeca-8,10,14-trien-7-one

AU - Chong, Daniel J W

AU - Chong, Florence H L

AU - Latip, Jalifah

PY - 2016/6/1

Y1 - 2016/6/1

N2 - This paper reports the improved procedure for aldol condensation between citral and 2-octanone with Amberlyst A-26 OH to give 11,15-dimethyl-hexadeca-8,10,14-trien-7-one. The improved synthesis utilizing Amberlyst A-26 OH as the solid catalyst produces better yield (93.0%) and enables simple work-up procedure. The experimental conditions are evaluated and optimized at 2-octanone/citral molar ratio of 10, catalyst amount of 5% (mole of citral), and temperature of 60°C in 3.5 h reaction time. 11,15-Dimethyl-hexadeca-8,10,14-trien-7-one is isolated using preparative thin layer chromatography with hexane:ethyl acetate (9.5:0.5) and confirmed by gas chromatography-mass spectrometry (GC-MS), ultraviolet-visible (UV-Vis), Fourier transform infrared (FTIR) and nuclear magnetic resonance (NMR).

AB - This paper reports the improved procedure for aldol condensation between citral and 2-octanone with Amberlyst A-26 OH to give 11,15-dimethyl-hexadeca-8,10,14-trien-7-one. The improved synthesis utilizing Amberlyst A-26 OH as the solid catalyst produces better yield (93.0%) and enables simple work-up procedure. The experimental conditions are evaluated and optimized at 2-octanone/citral molar ratio of 10, catalyst amount of 5% (mole of citral), and temperature of 60°C in 3.5 h reaction time. 11,15-Dimethyl-hexadeca-8,10,14-trien-7-one is isolated using preparative thin layer chromatography with hexane:ethyl acetate (9.5:0.5) and confirmed by gas chromatography-mass spectrometry (GC-MS), ultraviolet-visible (UV-Vis), Fourier transform infrared (FTIR) and nuclear magnetic resonance (NMR).

KW - 2-octanone

KW - aldol condensation

KW - Amberlyst A-26 OH

KW - citral

KW - pseudoionone

UR - http://www.scopus.com/inward/record.url?scp=84973569685&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84973569685&partnerID=8YFLogxK

U2 - 10.1515/gps-2015-0126

DO - 10.1515/gps-2015-0126

M3 - Article

VL - 5

SP - 297

EP - 304

JO - Green Processing and Synthesis

JF - Green Processing and Synthesis

SN - 2191-9542

IS - 3

ER -