The document summarizes the Perkin reaction, which involves converting an aromatic aldehyde and an anhydride to an α,β-unsaturated carboxylic acid using a base catalyst such as sodium acetate. The reaction proceeds via an E1cb mechanism, which is a two-step process where a base abstracts a proton to form a stabilized anion, whose lone pair of electrons then moves to the neighboring atom to expel a leaving group and form a double bond. Some applications of the Perkin reaction include synthesizing coumarin and the anticoagulant drug warfarin.

1. Perkin reaction
PREM (2015A5PS862H)
BITS PILANI HYDERABAD CAMPUS

2. 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

3. SCHMETIC OF PERKIN REACTION:
• Reagents: Aromatic aldehyde, anhydride, Sodium acetate
(NaOAc), base and acid work-up.
• Product: alpha-beta unsaturated carboxylic acid

4. E1cb mechanisms:
• 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

5. 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

6. Mechanisms:

7. Applications
• In 1868, Perkin reported the synthesis of coumarin by the
reaction of sodium salt of salicylaldehyde with Ac2O.
• anti-inflammatory, anti-oxidant, anti-allergic, anti-viral and anti-
carcinogenic activities

8. Warfarin
• anticoagulation (clot formation inhibition) in areas of
slowly running blood (such as in veins and the pooled
blood behind artificial and natural valves)

9. Mechanisms of action
• Does not affect thickness or viscosity of blood
• Decreases the proteins which allows blood to clot

10. • Poly(dihydroferulic acid) ,a bio renewable
thermoplastic copolymer

11. Thank you