Indeno-fused Naphthol Synthesis via Succinic Acid Intermediate
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Solution Overview
Problem
The existing methods for synthesizing indeno-fused naphthol materials, such as photochromic indeno-fused naphthopyrans, result in low yields and high costs due to the complexity of the Stobbe reaction route, which involves separating a mixture of indeno-fused naphthols, leading to economic and efficiency challenges.
Innovation Solution
A method involving the reaction of an alkyl benzene with maleic anhydride to form a succinic acid intermediate, which is then converted to an indanone acid intermediate and subsequently reacted with a nucleophile to produce indeno-fused naphthol, offering improved yield and economic benefits.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Ease of manufacture
If the Stobbe reaction route is used to synthesize indeno-fused naphthol materials, then the synthesis can be performed with established methodology, but the yield is reduced and costs increase due to the need to separate mixtures
Solution Approach 1:
The invention extracts and eliminates the problematic mixture formation step from the synthesis route. By using a different reaction pathway that directly produces the desired indeno-fused naphthol isomer without forming mixtures, the need for separation is removed entirely, thereby maintaining ease of manufacture while dramatically improving yield
Solution Approach 2:
Instead of using the conventional Stobbe reaction that produces mixtures requiring separation, the invention inverts the approach by employing a reaction sequence that inherently produces the desired product in high purity. This involves forming a cyclic ketal intermediate first, then performing nucleophilic substitution to directly obtain the target compound without isomer mixture formation
2Ease of manufacture
If the Stobbe reaction route is used to synthesize indeno-fused naphthol materials, then the synthesis can be performed with established methodology, but the costs increase due to separation and isolation steps
Solution Approach 1:
The invention extracts and eliminates the problematic mixture formation step from the synthesis route. By using a different reaction pathway that directly produces the desired indeno-fused naphthol isomer without forming mixtures, the need for separation is removed entirely, thereby maintaining ease of manufacture while dramatically improving yield
Solution Approach 2:
The invention eliminates the need to discard material through separation processes. By designing a reaction pathway that produces the desired product directly without forming mixtures, all starting materials are converted to the target compound, maximizing material utilization and eliminating losses associated with separation and isolation steps
3Manufacturing precision
If separation and isolation steps are performed to isolate desired indeno-fused naphthol, then the purity of the product is improved, but the yield is significantly reduced
Solution Approach 1:
Instead of using the conventional Stobbe reaction that produces mixtures requiring separation, the invention inverts the approach by employing a reaction sequence that inherently produces the desired product in high purity. This involves forming a cyclic ketal intermediate first, then performing nucleophilic substitution to directly obtain the target compound without isomer mixture formation
Solution Approach 2:
The invention extracts and eliminates the problematic mixture formation step from the synthesis route. By using a different reaction pathway that directly produces the desired indeno-fused naphthol isomer without forming mixtures, the need for separation is removed entirely, thereby maintaining ease of manufacture while dramatically improving yield
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 method enhances the yield of indeno-fused naphthol materials and reduces synthesis costs by simplifying the process and increasing the efficiency of the reaction steps, providing a more economical route to these valuable compounds.
Implementation Method 1
reacting an alkyl benzene with maleic anhydride to form a succinic acid intermediate
Implementation Method 2
converting the succinic acid intermediate to an indanone acid intermediate
Implementation Method 3
reacted with a nucleophile to produce indeno-fused naphthol
Data Source
AI summary
The present invention relates to a method of making indeno-fused naphthol materials, that involves, with some embodiments, forming an indanone acid intermediate, represented by the following general Formula V,With Formula V, m is from 0 to 4, and R1 for each m, Rg and Rh can each be independently selected from, for example, hydrogen and hydrocarbyl.