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Synthesis Of E,E-Dibenzalacetone (E,E-DBA)

Genevieve Murstig
October 29, 2015

Abstract
The purpose of this experiment was to synthesize a E,E-Dibenzalacetone (E,E-DBA) making use of a base-

catalyzed aldol condensation and to characterize crude and purified samples of E,E-DBA by melting point

determination. Referencing Table 1, the resulting yield was 106.3% for the crude sample and 28.5% for the purified

sample. Isolation, separation and purification of the crude and purified products of E,E-DBA was made possible via

solid-liquid extraction and recrystallization via vacuum filtration (using a Hirsch funnel). Purity of the product was

determined by visual inspection and by using a Mel-Temp device to evaluate the samples melting point versus the

literature value for E,E-DBA. Incorrect visual cues and melting point values determined for E,E-DBA crude was at

73-75C and 78-80C for purified products thus characterizing an impure product.

Introduction
The reaction mechanism is demonstrated in Scheme 1 below. The goal of this experiment was to employ a

based-catazlyed aldol condensation of the reaction of acetone, a ketone, and dibenzalaldehyde, an aldehyde, in the

synthesis of E,E-dibenzalacetone and to characterize the crude and purified samples of E,E-dibenzalacetone by

melting point determination. The final purified E,E-DBA product should theoretically produce .2878 grams,.0012

moles of pure crystals of the product and a melting point between 110-111 C, allowing only a range of +/- 2 from

the literature value. The balanced chemical equation for the synthesis of E,E-DBA is as shown below in Scheme 1.

Scheme 1
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Results
The results of the synthesis of E,E-Dibenzylacetone are summarized in Table 1.

Table 1. Synthesis Of E,E-Dibenzylacetone

molar volume/mass yield mp

Compound mass moles (C)
(g/mol)

benzaldehyde 106.12 g/mol .250 mL N/A N/A

(density 1.043 g/mL) .261 g
.02457 moles

acetone 58.08 g/mol .100 mL N/A N/A

(density 0.788 g/mL) .079 g
.00136 moles

E,E-DBA 234.29 g/mole N/A .0278 g 110-111 C

(a yellow solid) .0012 moles
(theoretical yield) (literature value)

E,E-DBA 234.29 g/mole N/A .306* g; 106.3% 73-75C

(a yellow solid) (crude) (crude)

.082* g; 28.5% 78-80C

(purified) (purified)

*yellow powder

Discussion

The synthesis of E,E-DBA was prepared by combining the following: .250 mL of benzalaldehye, .100 mL

of reagent grade acetone, .5 mL of 95% ethanol and 1 mL of a pre-prepared catalyst solution into a 10 mL round

bottom (RB) flask. Refer to Scheme 1 for the balanced equation. The catalyst solution was prepared by dissolving

10 grams of sodium hydroxide in 100 mL of water and 75 mL of 95% ethanol. The sodium hydroxide is the base and

acts as the catalyst in this reaction. This catalyst solution is used to speed up the product of the reaction to precipitate

out of solution. A microscale condenser is then attached to the top of the RB flask and the light yellow fluid is gently
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swirled for 15 minutes. A tightly secured connection of the microscale and flask allows the interior to be vacuum

tight and prevents any escape of vapors. After 15 minutes, it is observed that the yellow fluid has turned to a wet

bright yellow pudding-like solid. As described by the instructor, the clear fluids will turn yellow and finally achieve

a yellow solid which would be indicative of a proper E,E-DBA product. Based on the IUPAC Gold Book, this is due

to a process called halochromism; a color change that occurs at the addition of an acid, base, or salt to a solution

changes it from colorless into a colored compound. The ethanol, in this case, is the acid. This yellow, wet, solid

crude product of E,E-DBA was ready for filtration.

Vacuum filtration is used to quickly and completely separate a solid from the liquid in a solution; very

useful for this experiment. The microscale condenser is removed from the RB flask and isolation of the crude

product was filtered via a Hirsch funnel attached to a vacuum filter. The Hirsch funnel was equipped with a funnel

filter paper which allowed the solid E,E-DBA to be extracted from the liquid. De-ionized (DI) water was used to 1-

remove any remaining product out of the RB flask and 2-to gradually remove residual product from the sides of the

funnel. A total of 60 mL of DI water is used to retrieve the highest yield of crude product possible.

This slightly wet, seemingly identifiable, solid yellow, crude E,E-DBA powder is carefully removed from

the Hirsch funnel and placed into a pre-weighed 10 mL Erlenmeyer flask. The mass of the crude E,E-DBA product

was weighed at .306 g and a nice 106.3% yield, as referenced in Table 1. A very small sliver of the crude E,E-DBA

powder is placed into a small test tube for melting point determination later.

Purification of the crude E,E-DBA product is facilitated by recrystallization; this technique is used when

purifying solid compounds. An appropriate volume of 95% ethanol must be added to saturate the crude E,E-DBA.

Both products are placed into to a 10 mL Erlenmeyer flask. This ethanol is the solvent in which the crude E,E-DBA

will be dissolved. The solubility of E,E-DBA in ethanol is calculated at 1 mL/.4 g. Using the .306 grams of crude

E,E-DBA, the appropriate amount was calculated out to be .765 mL of 95% ethanol. Once combined, the flask with

product and the addition of two boiling stones were placed on a hotplate stirrer and performed under a fume hood,

for approximately 3 minutes allowing the product to be completely dissolved. The flask is carefully removed and to

be cooled, undisturbed, to room temperature to allow gradual cooling of the hot, saturated solution. To further

complete the recrystallization process, the flask is placed into a water bath. This slow cooling process promotes slow

crystal growth and the formation of a pure crystal product. Unfortunately, the flask was slightly warm when placed

into the bath promoting the formation of smaller, less pure crystals. Vacuum filtration using the Hirsch funnel was

once again performed on the E,E-DBA product. Removal of residual product in the flask was performed by using 6
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mL of chilled 95% ethanol. After filtration was complete, the wet, yellow powdery E,E-DBA product stayed in the

Hirsch funnel for one week to provide an opportunity for the crystals to dry thoroughly.

After one week, with very few crystals, the yellow still-powdery and wet E,E-DBA was carefully removed

from the Hirsch funnel and placed into a pre-weighed sample vial. At this point, the purified E,E-DBA product

should have created a crystalline product and by visual examination, it was evident that the product after this

recrystallization was not completely crystallized. Melting point determination will be the final determining

characterization factor. The mass of the E,E-DBA product was weighed at .082g, yielding only a 28.5% yield. This

low yield could have been due to too much solvent being used prior to the dissolving, the vacuum filtration being

performed prior to complete crystallization, or due to the inability of separating the wet product from the funnel and

paper.

Final assessment of the E,E-DBA product was performed by melting point determination. The E,E-DBA product

was prepared by placing a few crushed crystals of product onto a clean microscope slide and the crystals were

scraped into a capillary tube using a microspatula. No more than 1 mm was scraped into the tube. The crude E,E-

DBA from the test tube was also placed into a capillary tube using the same method. Melting point determination

was performed at a Mel-temp device which is used to monitor the crystal compounds from a solid to liquid state.

The melting point is a useful method in determining the purity of a compound and its identity. The melting point can

be influenced by the presence of impurities in the compound. The rate of heating is controlled by a variable

transformer and its rate of heating should be 1-2C per minute. As stated on Table 1, the melting point for the crude

E,E-DBA product was 73-75C and the purified E,E-DBA product was 78-80C. This very low melting point was

quite possibly due to the incremental increase of heat more than 1-2 per minute thus placing too much heat onto the

sample at once.

When initially determining the purity of the final E,E-DBA product, based on the website for Organic Synthesis, the

color was yellow as predicted, however, the wet, yellow powder had very few crystals and the large melting point of

78-80 that was more than 2 from the literature value of 110-11C. It is very evident that the final product is impure.

Experimental Procedures
The preparation was carried out according to the prescribed method.
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References
Laboratory Techniques in Organic Chemistry, Fourth ed. W.H. Freeman, 2014. Print.

IUPAC. Compendium of Chemical Terminology, 2nd ed. (the "Gold Book"). Compiled by A. D. McNaught and A.
Wilkinson. Blackwell Scientific Publications, Oxford (1997). XML on-line corrected version: http://
goldbook.iupac.org (2006-) created by M. Nic, J. Jirat, B. Kosata; updates compiled by A. Jenkins. ISBN
0-9678550-9-8. doi:10.1351/goldbook.

Org. Synth. 1932, 12, 22. DOI: 10.15227/orgsyn.012.00