One-Pot Synthesis of 3-Substituted 2-Vinylphenylsulfonates
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Solution Overview
Problem
Current methods for producing 3-substituted 2-vinylphenyl sulfonates face challenges with low overall yield and low atom economy, requiring multiple steps and unsuitable solvents like DMSO, which are not industrially viable.
Innovation Solution
A process involving the reaction of a compound of formula (II) with an activator and a base to form a compound of formula (III), followed by reaction with a compound of formula (IV) in the presence of a base, to produce 3-substituted 2-vinylphenyl sulfonates, utilizing thionyl chloride or phosgene as activators and recycling bases for improved yield and reduced waste.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Productivity
If conventional multi-step synthesis methods are used to produce 3-substituted 2-vinylphenylsulfonates, then the desired product can be obtained, but the overall yield is low and atom economy is poor
Solution Approach 1:
The patent combines multiple reaction steps into a single one-pot process. The condensation reaction of 3-substituted 2-(1-hydroxyethyl)phenols with carbonyl compounds followed by elimination of water to form vinylphenylsulfonates is achieved in one continuous operation without isolating intermediates, thereby improving overall yield and atom economy by eliminating material losses between steps
Solution Approach 2:
The reaction process is segmented into distinct phases within the one-pot system: initial condensation phase, intermediate formation phase, and elimination phase. This allows optimization of conditions for each transformation while maintaining continuous flow and avoiding intermediate isolation, resolving the contradiction between yield and atom economy
2Productivity
If conventional synthesis routes are used, then 3-substituted 2-vinylphenylsulfonates can be produced, but multiple steps and purification steps are required
Solution Approach 1:
The patent merges the condensation reaction and elimination reaction into a single operational step. By using a one-pot methodology where the intermediate vinylphenylsulfonate is not isolated but directly subjected to elimination conditions, the number of discrete manufacturing steps is reduced while maintaining product quality
Solution Approach 2:
The process maintains continuous useful action by immediately proceeding from condensation to elimination without interrupting the reaction flow. The intermediate compound remains in the reaction medium and is directly converted to the final product, eliminating the need for separate purification and isolation steps that会增加 process complexity
3Adaptability or versatility
If reagents like DMSO are used in the synthesis process, then the reaction can proceed, but the method is unsuitable for industrial use
Solution Approach 1:
The patent changes the reaction parameters by replacing DMSO with alternative solvents or solvent-free conditions that are more suitable for industrial application. The condensation and elimination reactions are optimized to proceed in industrially acceptable media while maintaining high conversion and selectivity, thus resolving the contradiction between reaction applicability and industrial suitability
4Productivity
If thionyl chloride or phosgene are used as activators, then the yield is improved, but waste products are generated
Solution Approach 1:
The patent converts potentially harmful reagents into beneficial outcomes by using thionyl chloride or phosgene as activators that generate gaseous byproducts (SO2, HCl, CO2) which can be easily removed. The base used in the reaction serves dual purposes: neutralizing the acidic byproducts and promoting the elimination reaction, thereby converting harmful waste into manageable gaseous products that simplify purification
Solution Approach 2:
The process design allows for easy discarding of gaseous waste products (SO2, HCl, CO2) that evolve during the reaction. The base byproducts can be recovered or neutralized in standard aqueous workup procedures, making the process more environmentally friendly despite using potent activators
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 achieves high yields with fewer steps and improved atom economy, using cheaper reagents and minimizing waste, making it suitable for industrial-scale production.
Implementation Method 1
reacting the compound of the formula (II) with an activator selected from the group consisting of thionyl chloride, phosgene, diphosgene, triphosgene, thiophosgene and chloroformic esters, in the presence of a base to give a compound of the formula (III)
Implementation Method 2
in the presence of a base to give a compound of the formula (III) is implemented, and (b) the combination of the formula (III) in the presence of a base with a compound of the formula (IV)
Implementation Method 3
subsequently eliminating water
Implementation Method 4
only one equivalent of gaseous substances (SO2, CO2) is produced instead of one equivalent of methanesulfonic acid
Data Source
AI summary
The invention relates to a method for producing 3-substituted 2-vinylphenylsulfonates.