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SYNTHESIS OF THE INSECT REPELLANT DEET

(adapted from Knoess & Neeland, J. Chem Ed 75, 1267(1998))

Insects and other animals often communicate using their sense of smell. For example,
female insects secrete small organic molecules into the air that serve as attractants to their male
counterparts. There is considerable evidence that mammals, including humans, communicate this
way as well. Chemicals can also serve a protective function. Dr. Dussourd of the UCA biology
department has shown that some plants secrete chemicals that discourage insects from feeding on
the plants. We often use chemicals to ward off unwanted critters. Citronella is a natural
substance used to repel insect pests (often it is put in candles). DEET is a synthetic chemical
used in commercial insect repellants such as OFF and Deep Woods. We will make DEET in this
laboratory exercise by converting an acid to an amide as shown below. The procedure is called
the Schotten-Bauman technique and is a generally useful method for synthesis of amides.
O O O
C C CH2CH3 C CH2CH3
OH Cl N
SOCl2 NH CH2CH3
CH2CH3

CH3 CH3 CH3

m-Toluic Thionyl m-Toluoyl chloride N,N-Diethyl-m-touamide


acid Chloride (DEET)
MW 136.15 118.98 154.60 191.27
mp 111-113
(°C)
bp (°C) 139.7 865mm 1111mm
sp. gr. 1.65615 0.996
nD20 1.5212

Experimental Procedure:

CAUTION: Ether (flammable), pyridine (smelly), and thionyl chloride (corrosive) are all volatile liquids.
Take care not to release the fumes from these substances into the laboratory air.

In a loosely stoppered 5-mL round-bottom flask under an aspirator “mini-hood” stir (for
10 minutes) a mixture of 0.5 g (3.7 mmol) of m-toluic acid, 0.2 mL of dry ether, 0.2 mL of
pyridine, and 0.55 mL (7.6 mmol) of thionyl chloride. After the reaction is complete, connect the
flask to a water-aspirator vacuum (use a trap) for 10 minutes to remove the excess thionyl
chloride.

In a 50-mL conical flask cool a mixture containing 1.3 mL (12 mmol) of diethylamine
and 5 mL of 10% aqueous NaOH in an ice bath. Pipet the acid chloride solution prepared above
into the amine mixture. Stir this mixture for five minutes. Use a separatory funnel to remove the
DEET from the reaction mixture by extracting three times with 10 mL portions of diethyl ether.
Dry the combined ether extracts over Mg SO4, then filter them into a tared beaker or vial.

Add 1 mL of toluene to the boiling flask and then evaporate the solvent. (The toluene
removes the water and pyridine azeotropically-what is an azeotrope?). At this point you should
be left with a clear pale yellow oil which is DEET. Determine the mass of your product and
calculate a percent yield based on the initial quantity of the limiting reagent. Analyze your
product by gas chromatography, infrared spectroscopy, and/or NMR spectroscopy as directed by
your laboratory instructor.