Perkin Reaction

PREM
2015A5PS862H
Introduction
The Perkin reaction is an organic reaction used to convert an aromatic
aldehyde and an anhydride to an α,β-unsaturated carboxylic acid
It is aldol condensation of an aromatic aldehyde and an acid anhydride
(which contain alpha hydrogen), in the presence of an alkali salt of the
acid.
The alkali salt acts as a base catalyst, and other bases can be used
instead.
as sodium acetate or potassium carbonate
 The regiochemistry of the reaction, the relative position of the
carboxylic acid and aromatic ring in the final product, can be either E
or Z

SCHMETIC OF PERKIN REACTION:

Reagents: Aromatic aldehyde, anhydride, Sodium acetate (NaOAc),
base and acid work-up.
Product: alpha-beta unsaturated carboxylic acid
E1cb elimination:
When the poor leaving group (such as -OH or -OR) and another atom
(typically a hydrogen) leave the molecule and no new atoms are added
Occurs in basic condition
Two species have therefore been eliminated
An elimination results in the formation of a new π bond
 E1cB is a two-step process
First, a base abstracts the most acidic proton to generate a stabilized anion
The lone pair of electrons on the anion then moves to the neighbouring atom,
thus expelling the leaving group and forming double
Mechanism:
 Why isn't Perkin reaction possible
with aliphatic aldehydes?
Consider Perkins reaction of benzaldehyde with acetic anhydride to form
cinnamic acid.