To prepare phenyl benzoate from phenol and benzoyl chloride by Schotten Baumann reaction.
Apparatus & Chemical Required:-
To prepare phenyl benzoate to phenol, you will need the following materials:
- Phenyl benzoate
- Water
- Sulfuric acid (H2SO4)
- Sodium hydroxide (NaOH)
- A round-bottomed flask
- A reflux condenser
- A heating source (such as a hot plate)
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Theory and principle:-
Phenyl benzoate can be converted to phenol through the process of hydrolysis, which involves breaking down a compound by reacting it with water.Phenol react with an aromatic acid chloride in the presence of excess NaOH reaction at room temperature to form an ester is called as Schotten Bauman reaction.
If Phenol is shaken with benzoyl Chloride and excess amount of sodium hydroxide solution it is benzolyted to give the ester, phenyl benzoate. The phenol is converted into ionic compound sodium phenoxide by dissolving it sodium hydroxide solution.
General reaction :-
Mechanism for this reaction:-
Procedure:-
Here is the procedure you can follow:
- Set up the round-bottomed flask with a reflux condenser.
- Add a small amount of water (around 50 mL) to the flask.
- Add a small amount of sulfuric acid to the water. The amount of sulfuric acid should be equal to about 1/10th of the weight of the phenyl benzoate.
- Slowly add the phenyl benzoate to the flask, being careful to avoid splashing.
- Heat the mixture using the heating source until it reaches a boiling point.
- Slowly add sodium hydroxide to the mixture, being careful to avoid splashing. The amount of sodium hydroxide should be equal to about 1/2 of the weight of the phenyl benzoate.
- Allow the mixture to cool to room temperature.
- Separate the phenol from the mixture by carefully pouring the mixture through a filter.
- Wash the phenol with a small amount of water to remove any impurities.
- Collect the purified phenol and store it in a clean container.
Precaution-
This procedure can be dangerous, as it involves the use of hazardous chemicals. It is important to follow all safety guidelines and wear appropriate protective equipment.
1- Always wear gloves while handling chemicals.
2- Wear goggles to protect Eyes
3- Benzoyl chloride should be handled with care under a fumehood.
4- Phenol is not only toxic but will cause serve burns
5- Use freshly prepared solution of NaOH.
Result:-
1- Yield of crystals =
2- Colour of Crystal = colorless
3- Observed melting point of crystals =
4- Literature melting point of compound =
Question Asking In Exam :-
Schotten-Baumann reaction :-
The Schotten-Baumann reaction is a chemical reaction that converts amines to amides using formic acid or formamide as acylating agents. The reaction is named after German chemists Gustav Schotten and Paul Baumann, who reported it in 1906. The reaction is typically carried out in the presence of a base such as potassium carbonate or sodium hydroxide to neutralize excess formic acid and formamide formed during the reaction. The Schotten-Baumann reaction is useful for synthesizing amides from primary, secondary, and tertiary amines.
The general reaction equation for the Schotten-Baumann reaction is:
R-NH2 + HCOOH → R-CO-NH2 + H2O
Here, R represents a primary, secondary or tertiary alkyl group.
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to prepare phenyl benzoate from phenol
schotten baumaan reaction and mechanism
phenol to phenyl benzoate
