Schotten Baumann reaction-mechanism-application-Schotten Baumann reaction-phenol-aniline.

Schotten Baumann reaction .

The benzoylation of phenol is carried out in presence of aqueous NaOH  or pyridine solution . Because , Benzoyl chloride does not hydrolysed by base .

So, the benzoylation of phenol in presence of aqueous NaOH  solution gives phenyl acetate . This  reaction is known as Schotten Baumann reaction.

There are few another reaction of phenol and aniline which  are also know as Schotten Baumann reaction . Such as acylation of phenol and aniline in presence of pyridine base . 

Schotten Baumann reaction is a very important aromatic nucleophilic substitution bimolecular reaction .The reaction occurs via tetra hedral intermediate .

Schotten Baumann reaction of  phenol :

The Schotten Baumann reaction of phenol occurs in presence of acetyl chloride and pyridine base or acetic anhydride with pyridine base . The Schotten Baumann reaction of phenol is shown below .

Schotten Baumann reaction of aniline :

The Schotten Baumann reaction of aniline occurs in presence of acetyl chloride and pyridine base or acetic anhydride with pyridine base . The Schotten Baumann reaction of aniline is shown below .

Schotten Baumann reaction mechanism:

Schotten Baumann reaction is a very important aromatic nucleophilic substitution bimolecular reaction . The reaction occurs via tetra hedral intermediate .

Schotten Baumann reaction mechanism regarding phenol and aniline occurs via tetra hedral intermediate,are shown below.

Schotten Baumann reaction mechanism regarding phenol by using acetyl chloride and acetic anhydride reagents.

Schotten Baumann reaction mechanism regarding phenol by using acetyl chloride .

Schotten Baumann reaction application:

The Schotten Baumann reactions are widely used today in organic chemistry .

For example, Schotten Baumann reaction is used to synthesis N-vanillyl nonanamide , benzamide from benzoyl chloride and a phenethylamine. 

It is also used for acylation of benzyl amine with acetyl chloride or acetic anhydride.

There are few another example application of Schotten Baumann reaction regarding phenol and aniline . Such as nitration, bromination, Friedel crafts alkylation and acylation reaction .

Nitration of both aniline and phenol in presence of concentrated nitric acid and concentrated sulfuric does not occur . 

Because , in such cases instead ofnitration ,oxidation occur . So the expected products are unavailable .

Again , bromination of phenol and aniline in presence of water gives poly bromo aniline or poly bromo phenol ,instead of mono bromo aniline or phenol .

In the similar way aniline and phenol does not participate in Friedel crafts alkylation or acylation reaction .

We can overcome all the above said problem by applying Schotten Baumann reaction and so nitration , bromination, Friedel crafts alkylation and acylation of phenol and aniline occurs easily by using the usual reagents.

Schotten Baumann reaction also prevent the poly bromination of phenol and aniline.

Summary:

Schotten Baumann reaction .

Schotten Baumann reaction of  phenol .

Schotten Baumann reaction of aniline .

Schotten Baumann reaction mechanism.

Schotten Baumann reaction application.

Pyridine is more basic than aniline