Chromanone Synthesis via Halobenzene Substitution
Find Innovative SolutionsGenerate Solutions
Solution Overview
Problem
The high cost of substituted phenols used in synthesizing chromanone derivatives increases the expense of producing these compounds, necessitating a more cost-effective method for their preparation.
Innovation Solution
A method involving the reaction of substituted halobenzene with an alcohol in the presence of a base and a catalyst, followed by oxidation and cyclization, which uses cheaper halobenzene instead of phenol, thereby reducing production costs and improving yield.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Ease of manufacture
If substituted phenols are used as raw materials for preparing substituted chromanone derivatives, then the synthesis can proceed through conventional methods, but the production cost increases due to the high expense of substituted phenols
Solution Approach 1:
The patent replaces expensive substituted phenols with cheaper substituted halobenzenes as raw materials. This substitution directly addresses the cost issue by using more economical starting materials while maintaining the ability to synthesize the desired chromanone derivatives through a modified reaction pathway involving nucleophilic aromatic substitution.
Solution Approach 2:
The patent changes the chemical parameters of the raw materials from phenolic compounds to halobenzene derivatives. This parameter change in the starting material structure enables cost reduction while achieving the same synthetic objective through different reaction mechanisms and conditions.
2Ease of manufacture
If substituted phenols are used as raw materials, then the synthesis pathway is conventional, but the yield and efficiency of preparing substituted chromanone derivatives are reduced
Solution Approach 1:
By using substituted halobenzenes instead of substituted phenols, the patent not only reduces cost but also improves reaction efficiency. The halobenzene-based pathway provides better yields and faster reaction rates, directly enhancing productivity while maintaining synthetic accessibility.
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 effectively synthesizes chromanone derivatives with high yields while avoiding the use of expensive phenols, thus reducing production costs and enhancing efficiency.
Implementation Method 1
The compound of formula (II) may be prepared by reacting a compound of formula (III) with a compound of formula (IV) in the presence of a catalyst and a base. The catalyst may include a ligand and a copper compound.
Implementation Method 2
3-(2-Fluoro-phenoxy)-propionic acid was dehydrated and cyclized in the presence of concentrated sulfuric acid to 8-Fluoro-4-chromanone
Implementation Method 3
3-(2-Fluoro-phenoxy)-propionic acid was dehydrated and cyclized in the presence of concentrated sulfuric acid to 8-Fluoro-4-chromanone
Data Source
AI summary
The present disclosure relates to a method for preparing a compound of formula (I).In the compound of formula (I), n may be 0 to 5 and each of R1, R2, R3, and R4 may be independently selected from the group consisting of H, —O-Alkyl, halo, alkyl, —CN, or —NO3.