Date- 05-12-2020

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REACTION OF THE DAY

Chemistry
Fries Rearrangement

The Fries Rearrangement enables the preparation of o- and p-acyl phenols from phenolic esters. The reaction
is catalyzed by Lewis acids such as AlCl3, BF3.

Mechanism of the Fries Rearrangement

After hydrolysis, the product is liberated.

Important point:
 The ortho/para product is dependent on the temperature. Low temperatures generally favor the para product
and high temperatures favour the ortho product.

 The R group may be aliphatic or aromatic.

 

(1)
 Try Yourself
Br
OMe O
1. Anhyd. AlCl3

O Ph–Cl 160°C
1. 2. H3O+/ Product
Br

OH
OH O OH Br

(1) (2) OH

Br Br O Br

OH OH

OH Br

(3) O (4) O
Br

Br Br OH



Answer of Question Based on Etard Reaction

1. Answer (2)

(2)