Aldol Condensation: Synthesis of Dibenzalacetone using the

Claisen-Schmidt Reaction

Abstract:
In this experiment, dibenzalacetone was prepared via an aldol condensation
reaction between acetone and benzaldehyde. Acetone and benzaldehyde were
mixed with sodium hydroxide and ethanol, and mixed vigorously for 30 minutes.
The crystals were rinsed with water then centrifuged. This was repeated a total
of three times. The dibenzalacetone was then characterized using melting point
analysis. The observed melting point was 93.5C- 109. 2C compared to a cited
value of 110C. The sample was not completely dry and could have contributed
to the lower and broader observed melting point. The percent yield was 117 %.
This percentage occurred because of the excess moisture in the sample.

Fig 1. Equation of Acetone and Benzaldehyde to form Dibenzalacetone

Introduction:
Dibenzalacetone, or DBA, is often used as an ingredient in sunscreen lotions and
sprays because it has spectral properties that make it capable of absorbing UV
light. It is also known to possess anti-inflammatory properties and can therefore

be used to treat pain, swelling and inflammation. 1 Dibenzalacetone can also be

used as a ligand in organometallic chemistry, and its derivatives are often utilized
as polymer crosslinkers.2
This experiment demonstrated the Claisen-Schmidt condensation of mixed
aldols. Enolate ions were formed when the molecules with hydrogens alpha to
carbonyl groups were reaction with a base (NaOH.)

Fig. 2 Acetone reaction and Sodium Hydroxide Reaction

When an enolate forms from an aldehyde, it normally reacts with unreacted
aldehydes to form an aldol addition/condensation. Ketones are less reactive
toward nucleophilic additions and therefore, the enolate formed from a ketone
can be used to react with an aldehyde. This is known as the Claisen-Schmidt
reaction. When the product formed still has a reactive alpha hydrogen and a
hydroxide adjacent to an aromatic ring, the reaction will quickly undergo
dehydration giving a condensation product.

Fig. 3 Claisen-Schmidt Reaction

Because of the symmetry of acetone, the reaction can now be repeated on the
other side of the carbonyl which then form the final product, dibenzalacetone.

Procedure:
0.2206g of benzaldehyde was transferred to a centrifuge tube. 1.6 ml of ethanol
and 2.0 ml of 3M sodium hydroxide were measured then transferred to the
centrifuge tube via clean, dry syringes. Using a micropipette syringe, 0.073 ml of
acetone were measured then injected into the centrifuge tube. The tube was
then capped, and shaken vigorously by hand for approximately 30 minutes.
The solution was then centrifuged for one minute on level one. The excess liquid
was removed with a pipette, and then rinsed with 3-4 ml of de-ionized water. The
centrifuge tube was capped and shaken, then placed back in the centrifuge again
for one minute on level one. This rinse procedure was completed twice.

After the final rinse and removal of excess liquid, the crystals were removed from
the centrifuge tube, placed on a filter in a sealed Hirsch filter, then vacuumed.
After vacuuming, the crystals were removed from the Hirsch filter and placed
between 6 paper filters to absorb the excess moisture. The crystals were then
weighed.
After weighing the crystals, the melting point was determined using a Vernier
melt station and Vernier LabQuest 2.

Results and Calculations:

Mass of product: 0.1646 g
Theoretical Yield: 0.1407 g
Percent Yield: 116.99%

Finding Limiting Reagent

Acetone 0.073mL | 1 mol A | 1 mole prdct | 224g prdct
| 58.08 g | 1 mol A
|
= 0.2815 g dibenzalacetone
Benzaldehyde 0.226 g B | 1 mol B | 1 mole prdct | 224g prdct
| 58.08 g B | 2 mol B |
= 0.4358 g dibenzalacetone
The limiting reagent for this reaction is acetone as it yields the least amount of
dibenzalacetone.

Aldol Condensation: Synthesis of Dibenzalacetone

Theoretical Yield
Acetone 0.073mL | 1 mol A | 1 mole prdct | 224g prdct
| 58.08 g | 1 mol A
|
= 0.2815 g dibenzalacetone
Percent Yield
(mass of DBA crystals)
(theoretical yield)

0.3294 g DBA
0.2815 g DBA

x 100 =

= 117.02% yield
Discussion and Conclusions:
In this experiment, an aldol condensation was carried out under basic conditions.
In these types of reactions, carbonyl compounds act as either the enolate ion or
the electrophile, or sometimes both. The carbonyl compound which becomes the
enolate ion must possess at least 1 -carbon. In this experiment, the enolate ion
originates from acetone because benzaldehyde lacks an -carbon.
Benzaldehyde, therefore, acts as the electrophile in this reaction. The enolate
ion derived from acetone then reacts with benzaldehyde to form a hydroxyketone. This -hydroxyketone will then undergo dehydration to form an
enome, a conjugated system of an alkene and a ketone. This product is also
called an ,-unsaturated ketone which is stabilized by conjugation with the
phenyl substituent. This ,-unsaturated ketone then undergoes a second aldol
condensation to give the final product, dibenzalacetone.

References
1

Smerbeck, R. V. & Pittz, E. P. (1986). U.S. Patent No. 4,587,260. Washington,

DC: U.S. Patent and Trademark Office.

Heidt, P. C. & Elliott M. L. (2001). U.S. Patent No. 6,194,615. Washington, DC:
U.S. Patent and Trademark Office.

http://1chemistry.blogspot.com/2011/11/objective-1.html

http://www2.volstate.edu/chem/2020/Labs/Aldol_Condensation.html