Experiment 5
Synthesis of Eugenol-5-Aldehyde
Group 1: Galace, Frauline Kathleen |
Malate,JhanelaJhane|Reyes, Myla|Rillo,Marcelina
Lab Instructor: Prof. Roland AmielPeñaloza
Eugenol
C10H12O2
• Eugenol occurs naturally in cloves, cinnamon, nutmeg and bay. The
name is derived from Eugeniacaryophyllata, a former scientific
name for cloves. It is extracted by Steam Distillation. It is used in
perfumeries, flavorings, essential oils and in medicine as a local
antiseptic and anesthetic. In a toothache drop preparation,
eugenol has an 85% [Link] is also used in formulating
insect attractants and UV absorbers, analgesics, biocides, and
antiseptics.
Limitations in the use of Eugenol: Different Preparations in the market
• Eugenol can be hepatotoxic, and it may containing Eugenol.
cause damage to the liver. • Clove oil has a local anesthetic effect
• Overdose is possible, causing a wide and temporarily numbs and relieves the
range of symptoms from blood in the pain
patient's urine, to convulsions, • Zinc-oxide eugenol is used in dentistry
diarrhea, nausea, unconsciousness, • Eugenol Oil Insecticide- insecticide
dizziness, or rapid heartbeat.
• Some people are sensitive to it when
used in perfumery. Eugenol can cause
an allergic reaction in humans including
rash, itching or shortness of breath.
• Eugenol can cause immunotoxicity
• When used in undiluted form, it causes
burning, nerve or tissue damage.
Experiment 5
Synthesis of Eugenol-5-Aldehyde
• I. Objective
• To synthesize eugenol-5-aldehyde from eugenol in glacial
acetic acid and hexamine.
• II. Discussion
• Eugenol, 4 –Allyl-2-methoxyphenol is obtained primarily from
clove oil. It is slightly soluble in water but it is miscible with alcohol
and other organic solvents. The para-allyl and ortho-methoxy
groups contribute to the antiseptic and anesthetic activity of the
phenolic group. It can be directly applied on a piece of cotton to
relieve toothaches. It is also used as a mouthwash because of its
antiseptic property and its pleasant taste.
• Eugenol Classification: Analgesic, Anti-infective, Insect attractant,
Repellent
Procedure
Roles of the Reagents: Identification Tests(Theoretical)
• Concentrated HCl – used as an A. Physical Tests
acidifying agent • 1. Color: Colorless or pale yellow
• Ether – used as an extraction solvent • 2. Odor: Spicy, clove-like aroma
• 20 % Sodium Hydroxide – used as an • 3. Specific gravity:1.06
alkalinizing agent • 4. Melting point:-9°C
• Strong aqueous sodium bisulfate – used
as a decolorizing agent
B. Chemical Tests
• Ferric Chloride T.S – used to detect
presence of phenols • 1. Solubility
• Water- slightly soluble
• Alcohol- soluble
• Ether- soluble
• Acetone: soluble
• 2. Reaction with 10% Sodium Hydroxide
It readily dissolved with the 10% NaOH and the solution soon deposited yellow
crystals of the sodium salt.
3. Reaction with Ferric Chloride
Deep blue coloration of the solution was observed.
Glacial Acetic Acid (excess) Hexamine (rate limiting)
(1.05g/cm3)(75mL)=78.75g 40g/140.19g/mol
==0.2853
No. of moles of limiting reactant= weight of the reactant/ MW of the reactant
= 78.75g/60.05g/mol
=== 1.3114
Theoretical yield= (no. of moles of LR) X (MW of the product)
= (0.2853) X (164+29)
= (0.2853)(193.2)
== 55.12
Experiment 6
SYNTHESIS OF ACETANILIDE
I. Objective
• To synthesize acetanilide from aniline, hydrochloric acid,
and acetic acid.
II. Discussion
• Acetanilide, a monoacetyl derivative of aniline is
prepared by heating aniline and acetic acid for several hours.
Acetanilide is a neutral compound and will not dissolve in
either acids or alkalis. It can be recrystallized from hot water.
• 2. Odor: Odorless
• 3. Appearance: white solid w/ a
flaky appearance
• 4. Melting Point: 114.3 degree
celcius
B. Chemical Tests
• 1. Hydrolysis of acetanilide
Identification Tests
A. Physical Tests
• 1. Color: . White, shining
crystalline leaflets
or white crystalline powder.
Acetanilide in Pharmaceuticals
This aniline derivative was the first one found to have
both analgesic and antipyretic properties. A. Cahn and
P. Hepp introduced this derivative into medical practice
under the brand name of Antifebrin in 1886. However,
the evident toxicity of this substance promoted the
need of searching for less toxic derivatives of aniline
like phenacetin. In 1948, it was discovered that
Acetanilide metabolizes into paracetamol in human
body and this resulting paracetamol had the analgesic
and antipyretic properties. As result, Acetanilide was
slowly replaced by its metabolite paracetamol which is
still quite well known in the pharmaceutical field.
Therapeutic uses: Side effects:
• 1. Used as fever-reducing agent ( anti- • Excessive or prolonged use engenders
pyretic) toxic side effects:
• 2. It was usedas analternative to • 1. it interferes with the function of
aspirin for many years intreating such hemoglobin, the oxygen-carrying
common complaints as headache, pigment of the blood.
menstrual cramps, and rheumatism. • 2. In the body acetanilide is mostly
(Analgesic) converted to acetaminophen, which has
• 3. Acetanilide is used as an inhibitor in replaced acetanilide in therapy because
hydrogen peroxide and is used to it is less likely to induce blood disorders.
stabilize cellulose ester varnishes. • 3. Highly toxic by ingestion. Causes
• 4. It is also a precursor in the synthesis cyanosis. 4. Skin contact and inhalation
of penicillin and other cause irritation.
pharmaceuticals.
