3-Hydroxybiphenyl Synthesis Using Base-Catalyzed Stepwise Reactions
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Solution Overview
Problem
There is a need for a novel method to produce 3-hydroxybiphenyl compounds and their derivatives efficiently.
Innovation Solution
A method involving the reaction of specific compounds in the presence of a base, followed by additional reactions with formic acid esters and methylating agents, to produce 3-hydroxybiphenyl compounds and derivatives.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Productivity
If conventional methods are used to produce 3-hydroxybiphenyl compounds, then the production process is simple, but the production efficiency is low and the yield is insufficient
Solution Approach 1:
The synthesis process is divided into multiple discrete steps: (1) forming the biphenyl core through coupling reaction, (2) introducing the hydroxyl group at the 3-position, (3) adding functional groups at the 2-position. This segmentation allows each step to be optimized independently, improving overall efficiency while maintaining manageable complexity
Solution Approach 2:
The method employs preliminary protection and activation steps, such as forming protecting groups on the hydroxyl group before coupling reactions, and pre-functionalizing intermediates. This allows the main synthesis steps to proceed more efficiently with higher yields, as the molecular structure is prepared in advance with necessary reactivity and stability features
2Manufacturing precision
If conventional synthesis routes are used, then the number of steps is few, but the yield of the target compound is low
Solution Approach 1:
The method optimizes reaction parameters at each step, including temperature, solvent choice, catalyst concentration, and reaction time. By carefully controlling these parameters, the yield of each intermediate and final product is maximized, achieving high overall yield while maintaining efficient production through streamlined processes
3Quantity of substance
If existing production methods are used, then the process is straightforward, but the availability of 3-hydroxybiphenyl compounds for applications is insufficient
Solution Approach 1:
The synthesis method is designed as a continuous process with minimal isolation steps between reactions. Intermediates are carried forward directly to the next reaction step, eliminating time-consuming purification cycles and maximizing the quantity of product obtained. This continuous approach increases availability while maintaining ease of manufacture through automated or semi-automated flow processes
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
The method allows for the efficient production of 3-hydroxybiphenyl compounds and derivatives, enhancing their availability for applications such as control of plant diseases.
Implementation Method 1
reaction of specific compounds in the presence of a base
Implementation Method 2
additional reactions with formic acid esters and methylating agents
Data Source
AI summary
The present invention provides a novel method for producing a 3-hydroxybiphenyl compound, and a novel method for producing a derivative of 3-hydroxybiphenyl compound using the same. Specifically, the present invention provides a method for producing a compound represented by formula (3) [wherein: R1, R2, R3, R4, and R5 are identical to or different from each other, and each represents a hydrogen atom or the like; and R10 and R11 are identical to or different from each other, and each represents a hydrogen atom or the like] which comprises reacting a compound represented by formula (1) [wherein: R1, R2, R3, R4, and R5 are the same as defined above; and R6 represents a phenylsulfonyl group or the like] and a compound represented by formula (2) [wherein: the combination of R8 and R9 represents a combination wherein R8 represents CH2NR12R13 or the like, and R9 represents a hydrogen atom, or the like; R10 and R11 are the same as defined above; and R12 and R13 are identical to or different from each other, and each represents a hydrogen atom or the like] in the presence of 0.1 mol or more and 5 mol or less of a base relative to 1 mol of the compound represented by formula (1) to produce the compound represented by formula (3).