ALPHA

Journal in Organic Chemistry

Volume 3, Issue No. 4

Preparation of Dibenzalacetone and Identification of Mixed Aldol Condensation Product

Tiongson, Stephanie Claire M.1

Rejano, Sander Clyde
Cruz, Kathlia D.2
Tiongson, Rejano, CM134L/A7, School of Chemical, Biological and Material Engineering and Science, Mapua University

ABSTRACT
An aldol condensation reaction is named based on the product formed by the reaction of two aldehyde or an aldehyde and a
ketone in the presence of a weak base, that results in the formation of an alcohol group. This experiment aims to give a
visualization of aldol condensation mechanism via the preparation of dibenzalacetone and identification of mixed aldol
condensation product. Dibenzalacetone was synthesized by combining benzaldehyde and acetone with sodium hydroxide and
ethanol. The crude was recrystallized using 95% ethanol. The experiment was able to produce 0.54 grams of dibenzalacetone
out of the 1.137 grams theoretical yield. Mixed aldol condensation product was obtained by combining 1mL of butyraldehyde
and 12.5mL of 95% ethanol in an Erlenmeyer flask together with 2.02grams of benzophenone and 5.6mL of potassium hydroxide.
It is identified that the mixed aldol condensation of the butyraldehyde and benzophenone is 2-(Diphenylmethylidene) butanal
with a yield of 22.47%.

Keywords: aldol, mixed aldol, dibenzalacetone, 2-(diphenylmethylidene)butanal

INTRODUCTION

An aldol condensation reaction is named based on the product
formed by the reaction of two aldehyde or an aldehyde and a
ketone in the presence of a weak base, that results in the formation
of an alcohol group. Aldol condensation occurs when there is an
aldehyde bearing an alpha-carbon with a dilute base that gives off
the beta-hydroxy aldehyde called aldol. Crossed aldol
condensation or mixed aldol condensation happens between two
different carbonyl compounds in which one do not bear an alpha
hydrogen.
This experiment aims to give a visualization of aldol condensation
mechanism via the preparation of dibenzalacetone and
identification of mixed aldol condensation product.
EXPERIMENTAL SECTION
The reagents used in this experiment were benzaldehyde, ethanol,
toluene, acetone, anisaldehyde, 2-propanol, butyraldehyde,
benzophenone, sodium hydroxide and potassium hydroxide.
These reagents were all prepared prior to the experiment.
A. Synthesis of Dibenzalacetone
In a vial, 1mL of benzaldehyde and 0.36mL of acetone was placed
and stirred until a yellow precipitate was seen. 5mL of 5M NaOH
and 95% ethanol was added, and the mixture was continuously
stirred for 30-45 minutes at room temperature. The product was
filtered in a Buchner Funnel and was recrystallized using 95%
ethanol.
B. Identification of a Mixed Aldol Product from Condensation
of Butyraldehyde and Benzophenone
1mL of butyraldehyde was placed in an Erlenmeyer flask together
with 12.5mL of 95% ethanol. The mixture is thoroughly mixed upon
the addition of 5.6 mL of 2M potassium hydroxide. 2.02 grams of
benzophenone was then added to the mixture and it was mixed
until precipitate formed. The product was crystallized for 18
minutes in an ice bath. The precipitate formed was recrystallized
using 2-propanol.
RESULTS AND DISCUSSIONS
A. Synthesis of Dibenzalacetone
Dibenzalacetone was synthesized via aldol condensation. Aldol
condensation took place when an aldehyde and ketone in which
one bears an alpha-carbon is reacted with a weak base. The
mechanism below shows how acetone was activated with sodium
hydroxide. The activation of the acetone carbon will be used for the
nucleophilic attack to the carbonyl carbon of benzaldehyde. The
entire mechanism for the formation of dibenzalacetone is shown in
Figure 2.
Figure 1. Activation

1. CM134L-Student, School of Chemical, Biological, and Materials Engineering and Sciences, Mapua University (stiongson81@gmail.com)
2. CM134L-Professor, School of Chemical, Biological, and Materials Engineering and Sciences, Mapua University (kadecastro@mapua.edu.ph)
 Figure 3. IR Spectra Dibenzalacetone

The spectra shown above is of dibenzalacetone. Monosubstituted

aromatic ring is represented from 692 cm-1 to 760 cm-1. The C=O
bond is represented at 1737-1649 cm-1, it also represents the
ketone present in the molecule. From 3053-2958 cm-1 represents
sp2 carbon stretch.

B. Synthesis of 2-(Diphenylmethylidene) butanal

Mixed aldol condensation process involves a reaction between a
ketone and an aldehyde in which one of these molecules do not
bear an alpha carbon. In this experiment butyraldehyde and
benzophenone are the starting material. It is identified that the
crossed aldol condensation of the two mentioned reagents is 2-
(Diphenylmethylidene) butanal, structure shown in Figure 4.

Figure 4. 2-(Diphenylmethylidene)butanal

The non-alpha-carbon bearing carbonyl is benzophenone.

Butyraldehyde, on the other side, is activated via the addition of
potassium hydroxide. The mechanism below shows the formation
Figure 2. Formation of Dibenzalacetone of 2-(Diphenylmethylidene)butanal.

The successful formation of dibenzalacetone was made possible

via the reaction with excess benzaldehyde. The experiment was
able to produce 0.54 grams of dibenzalacetone out of the 1.137
grams theoretical yield. The results of the experiment are
presented below in Table 1.

Actual Yield 0.54 grams

Theoretical Yield 1.137 grams
Percentage Yield 47.49%
Table 1. Results

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 It is recommended to use higher amount of starting materials to
obtain greater yield of product. Following the procedure for the
synthesis properly and applying various techniques for purification
of the products is also a key in obtaining greater yield.

REFERENCES

1. Robertson, D. L., ( 2012, November 14). Aldol Condensation:

Figure 5. Formation of 2-(Diphenylmethylidene)butanal Preparation of Dibenzalacetone (1,5-Diphenyl-1,4-petadien-3-
one). Retrieved from http://home.miracosta.edu/dlr/211exp5.htm
The experimental results are shown below in Table 2. The
synthesis obtained 0.59 g of product. However, this amount of 2. Pujada R. & Brizuela J., (2016, December 8). The Aldol
product is still impure because of the unsuccessful recrystallization Reaction Synthesis, purification and NMR
that implies that the product could be liquid at temperature greater Analyiss of 1,5-diphenyl-1,4-pentadien-3-one.
than -50C. The IR spectra in Figure 6 represents 2-
(Diphenylmethylidene)butanal.
SUPPORTING INFORMATION
Actual Yield 0.59 grams
Theoretical Yield 2.6254 grams Reagents Structure
Percentage Yield 22.47%
Table 2. Results Benzaldehyde

Ethanol

Toluene

Acetone

Anisaldehyde

Figure 6. IR Spectra 2-(Diphenylmethylidene)butanal 2-Propanol

At 3053-3026 cm-1 an sp2 carbon-hydrogen bond is observed. At

760-692 cm-1 monosubstituted aromatic oop is visible. The
aromatic C=C bond is observable at 1626-1447 cm-1. NaOH

CONCLUSIONS AND RECOMMENDATIONS

The objectives of the experiment were successfully achieved. KOH

Effective synthesis of dibenzalacetone was obtained having a yield
of 0.54 g. Aldol and Mixed aldol condensation mechanisms were
also explained and the product of mixed aldol condensation was
identified as 2-(Diphenylmethylidene) butanal.

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 Butyraldehyde

Benzophenone

Table 3. Reagents

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