Synthesis of Cinnamaldehyde

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Vidallon, Mark Louis P. Date Performed: February 20, 2012 CHEM44.1 2L Date Submitted: March 12, 2012

Synthesis of Cinnamaldehyde

I. Introduction
Cinnamaldehyde, cinnamic aldehyde or 3-phenyl-2-propenal is the major constituent of cinnamon oil, extracted from several species of Cinnamomum (C. verum, C. burmanii, C. cassia), under the family Lauraceae, a group of evergreen trees. Cinnamon bark (particularly C. verum) yields 0.4-0.8% oil, which contains 60-80% cinnamaldehyde, 4-5% sesquiterpenoids (α-humulene, β-caryophyllene, limonene and others), eugenol, cinnamyl acetate, eugenol acetate, cinnamyl alcohol, methyl eugenol, benzaldehyde, benzyl benzoate, cuminaldehyde, monoterpenes (linalool, pinene,
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To characterize the synthesized product using its boiling point, results of simple chemical tests and derivatization reactions, along with the determination of the melting points of the hydrazones and comparison of the hydrazones using their RGB values.

II. Materials and Methods A. Reagents
The following are the reagents were used in the experiment:

15% sodium hydroxide solution
Sodium chloride
95 % ethanol solution
40% sodium bisulfite solution
2, 4-dinitrophenylhydrazine
Nitric acid

B. Apparatus and Equipment

The following are the apparatus and equipment were used in the experiment:
50-mL round-bottom flask
50-mL beaker
10-mL graduated cylinder
10-mL pipet
Pasteur pipet
Micro distilling flask
Test tubes
Evaporating dish
Bunsen burner
Watch glass
Iron ring
Iron clamp
Iron stand
Separatory funnel
Wire gauze
Hot plate
Electronic top loading balance
Fisher-Johns melting point apparatus

III. Schematic Diagrams C. Synthesis of Cinnamaldehyde

(in round-bottom flask)


- cool in ice bath

+ 3.00mL 15% NaOH

+ 0.50mL dropwise with swirling

+ 3.00mL 15% NaOH

+ 0.50mL dropwise with swirling

+ 3.00mL 15% NaOH + 0.68mL dropwise with swirling

- reflux for 10-15 minutes

- cool to room temperature

- cool in ice bath

- separate layers

Organic layer
, very minimal

(in 10-mL graduated cylinder)
Aqueous layer very minimal, unreacted

H2O with

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