Cross Metathesis Synthesis of Aldehydic Perfuming Intermediates
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Solution Overview
Problem
The perfumery industry faces challenges in accessing compounds that impart novel aldehydic notes, particularly for reconstituting the delicate floral odor of muguet, as existing methods using Grignard reagents or radical chemistry result in low yield and selectivity.
Innovation Solution
A cross metathesis process between commercially available compounds to produce 3-(cyclohex-1-en-1-yl) propanal derivatives, utilizing novel intermediates to achieve high yield and selectivity without toxic acrolein or crotonaldehyde.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Productivity
If Grignard reagents or radical chemistry are used to produce aldehydic compounds, then the compounds can be synthesized, but the yield and selectivity are low
Solution Approach 1:
The patent changes the chemical reaction parameters by replacing Grignard reagents and radical chemistry with cross-metathesis reaction conditions. This involves changing the catalyst system (using ruthenium-based metathesis catalysts), the reaction mechanism, and the stoichiometry to achieve high yield and selectivity for aldehydic compounds with muguet-floral odor.
Solution Approach 2:
The patent substitutes the mechanical/chemical system of Grignard reagents and radical chemistry with an organic metathesis reaction system. This replacement eliminates the need for toxic reagents while improving reaction efficiency, yield, and selectivity through a more controlled and predictable reaction mechanism.
2Ease of manufacture
If existing methods are used to access perfuming compounds, then the compounds can be produced, but the process is tedious and requires complex reagents
Solution Approach 1:
The patent extracts and eliminates the complex and tedious steps from existing synthesis routes. By using cross-metathesis reactions, the method removes the need for Grignard reagent preparation, radical initiation steps, and multiple protection/deprotection sequences, thereby simplifying the overall manufacturing process.
Solution Approach 2:
The patent segments the synthesis into simpler, modular cross-metathesis steps that can be performed under mild conditions. Each reaction step is independent and can be optimized separately, making the overall process easier to manufacture and scale while reducing the need for complex reagents and equipment.
3Productivity
If toxic acrolein or crotonaldehyde are used as intermediates, then the desired compounds can be obtained, but toxic substances are introduced into the process
Solution Approach 1:
The patent converts the harmful approach of using toxic acrolein or crotonaldehyde intermediates into a beneficial process by employing non-toxic cross-metathesis reactions. The metathesis catalyst system enables the same or better compound production without introducing toxic substances, thereby eliminating the harmful factors while maintaining or improving productivity.
Applied Scientific Principles
This section explains which scientific principles are used to turn an abstract innovation direction into a practical engineering solution.
Function Achieved in This Case
This process provides a straightforward and efficient route to valuable perfuming ingredients with high yield and selectivity, overcoming the limitations of existing methods.
Implementation Method 1
comprising a cross metathesis step, in the presence of a metathesis catalyst, between compound of the formula (IIa), (IIb) or (IIc) with compound of formula (III)
Data Source
AI summary
The present invention relates to the field of perfumery. More particularly, it concerns valuable new chemical intermediates for producing perfuming ingredients. Moreover, the present invention comprises also a process for producing compound of formula (I).