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Related Concept Videos

Nitriles to Amines: LiAlH4 Reduction00:55

Nitriles to Amines: LiAlH4 Reduction

4.1K
Nitriles are reduced to amines in the presence of strong reducing agents like lithium aluminum hydride through a typical nucleophilic acyl substitution. The reaction requires two equivalents of the reducing agent. The reducing agent acts as a source of hydride ions.
As shown below, the mechanism involves three steps. Firstly, the hydride ion acting as a nucleophile attacks the nitrile carbon to form an anion. In the second step, a second equivalent of the hydride ion attacks the anion to...
4.1K
α-Alkylation of Ketones via Enolate Ions01:10

α-Alkylation of Ketones via Enolate Ions

2.2K
Ketones with α protons are deprotonated by strong bases like lithium diisopropylamide (LDA) to form enolate ions. The anion is stabilized by resonance, and its hybrid structure exhibits negative charges on the carbonyl oxygen and the α carbon. This ambident nucleophile can attack an electrophile via two possible sites: the carbonyl oxygen, known as O-attack, or the α carbon, known as C-attack. The nucleophilic attack via the carbanionic site is preferred. This is due to the...
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Preparation of 1° Amines: Gabriel Synthesis01:28

Preparation of 1° Amines: Gabriel Synthesis

2.7K
Direct alkylation is not a suitable method for synthesizing amines because it produces polyalkylated products. Gabriel synthesis is the most preferred method to exclusively make primary amines. The method uses phthalimide, which contains a protected form of nitrogen that participates in alkylation only once to predominantly give primary amines.
Strong bases like NaOH or KOH deprotonate the phthalimide to form the corresponding anion, which acts as a nucleophile. Further, the anion attacks an...
2.7K
Acid Halides to Ketones: Gilman Reagent01:14

Acid Halides to Ketones: Gilman Reagent

3.2K
Lithium dialkyl cuprate, also known as Gilman reagents, selectively reduces acid halides to ketones. The acid chloride is treated with Gilman reagent at −78 °C in the presence of ether solution to produce a ketone in good yield.
As shown below, the mechanism proceeds in two steps. First, one of the alkyl groups of the reagent acts as a nucleophile and attacks the acyl carbon of the acid chloride to form a tetrahedral intermediate. This is followed by the reformation of the...
3.2K
Preparation of Aldehydes and Ketones from Carboxylic Acid Derivatives01:18

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2.9K
Aldehydes are more reactive than carboxylic acids and hence, can get over-reduced to alcohol in the presence of strong reducing agents. Therefore, carboxylic acids are inefficient in preparing aldehydes using LAH.
Carboxylic acid derivatives like acid chlorides and esters are more easily reducible than the corresponding acids. The derivatives reduce in the presence of mild reducing agents to give aldehydes. Aldehydes can also be prepared by Rosenmund reduction, that is, the reduction of...
2.9K
Acetals and Thioacetals as Protecting Groups for Aldehydes and Ketones01:24

Acetals and Thioacetals as Protecting Groups for Aldehydes and Ketones

4.8K
Acetals are formed by reacting two equivalents of alcohol with carbonyl compounds like aldehydes or ketones. Acetals are unaffected by bases, nucleophiles, oxidizing agents, and reducing agents. They serve as protecting groups for aldehydes and ketones. Acetals can be easily formed and also easily removed via mild acid hydrolysis.
In the presence of multiple functional groups, when selective reduction of one group over the other is desired, groups like aldehydes and ketones that form acetals...
4.8K

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Highly Stereoselective Synthesis of 1,6-Ketoesters Mediated by Ionic Liquids: A Three-component Reaction Enabling Rapid Access to a New Class of Low Molecular Weight Gelators
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γ-Unsaturated aldehydes as potential Lilial replacers.

Martin Schroeder1, Marion Mathys, Nadja Ehrensperger

  • 1Givaudan Schweiz AG, Fragrance Research, Überlandstrasse 138, CH-8600 Dübendorf, (phone: +41 44 824 22 43; fax: +41 44 824 29 26). martin.schroeder@givaudan.com.

Chemistry & Biodiversity
|October 21, 2014
PubMed
Summary

Researchers sought a safer alternative to Lilial, a fragrance ingredient. They synthesized novel aldehydes via Claisen rearrangements, identifying a promising lead compound with a similar scent but improved properties for perfumery applications.

Keywords:
Claisen rearrangementMuguetOdorantsSila substitutionStructureodor relationship (SOR)

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Area of Science:

  • Organic chemistry
  • Perfumery chemistry
  • Fragrance ingredient development

Background:

  • Lilial (3-(4-(tert-butyl)phenyl)-2-methylpropanal) is a high-tonnage perfumery ingredient with a lily-of-the-valley scent.
  • Lilial is classified as a CMR2 material, necessitating the search for safer alternatives.
  • The perfumery industry requires ingredients with specific olfactory profiles and substantivity.

Purpose of the Study:

  • To find a replacement for the fragrance ingredient Lilial.
  • To synthesize novel aldehydes with potential 'Lilial' odor profiles.
  • To investigate structure-odor relationships (SOR) for lily-of-the-valley scents.

Main Methods:

  • Synthesis of aldehydes using Claisen rearrangements of vinyl ethers and allyl ethers.
  • Alternative synthesis via coupling of terminal alkynes with allyl alcohols.
  • Preparation of derivatives and sila analogues of key compounds.
  • Olfactory evaluation of synthesized molecules to determine SOR.

Main Results:

  • 5,7,7-Trimethyl-4-methyleneoctanal (10) was synthesized and identified as a promising lead compound.
  • Compound 10 possesses an odor profile very close to Lilial, though with lower substantivity.
  • Higher molecular weight aldehydes were synthesized to enhance substantivity.
  • Structure-odor relationships were explored through the synthesis and evaluation of various derivatives.

Conclusions:

  • Novel aldehydes were successfully synthesized as potential replacements for Lilial.
  • The synthesized compounds offer a similar lily-of-the-valley scent profile.
  • Further research into derivatives and analogues can optimize substantivity and olfactory properties for perfumery applications.