Max Yield Phenolate Formation with Phenol

AI Thread Summary
Phenol forms phenolate with maximum yield under high pH conditions, as it is a weak acid. To achieve this, adding an excess of a strong base is essential. While sodium or potassium hydroxide is commonly used, employing sodium hydride as a stronger base can enhance the reaction, particularly in tetrahydrofuran at temperatures below 10°C. This controlled approach allows for optimal phenolate formation.
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under what circumstances phenol forms phenolate with max yield
 
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High pH - it is a weak acid.
 
I know it's a weak acid. I need to know circumstances of forming phenolate with max yield
 
High pH - add excess strong base.
 
I agree. If you are seeking extremes, you might want to add sodium hydride (a very strong base, not needed to prepare phenolate) instead of the commonly used sodium or potassium hydroxide in tetrahydrofuran under 10°C in a controlled manner.
 

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