Mike Diatte, Gabriel Lloyd, Dru Harness
Dr. Ablin
Organic Lecture Report
2/21/11
Sources/Physical Properties/Health Effects
Desk Reference : Physicians' Desk Reference 2009.
Montvale, NJ: Physicians' Desk
Reference, 2008. Print.
Popular site : http://en.wikipedia.org/wiki/Naproxen
Peer reviewed journal : "NAPROXEN." TOXNET . Web. 19 Feb. 2011.
<http://toxnet.nlm.nih.gov/cgi-bin/sis/search>.
The IUPAC name for Aleve (Naproxen) is (S)-6-methoxy-beta-methyl-2naphthaleneacetic acid. The structure for this compound is as follows:
Functional groups found in this compound include a carboxylic acid (-COOH), a methyl group (-CH
3
), and a methoxy group (-OCH
3
). Hydrogen bonding is found within the carboxylic acid group due to the presence of the O-H. A C=O bond is found within the carboxylic acid, and C-O bond is found in the methoxy group. Carbon-carbon double bonds are within the naphthalene rings. There is one chirality center in the molecule, located at the carbon adjacent to the carboxylic acid.
The CAS number for this molecule is ( 22204-53-1).

IR Spectra:
(S)-6-methoxy-beta-methyl-2-naphthaleneacetic acid

Molecular weight = 230.26
Formula = C14H14O3
This compound is odorless and has a white to off-white crystalline substance. It is lipid soluble, practically insoluble in water at low pH and freely soluble in water at a high PH.
Aleve is a non-steroidal anti-inflammatory drug that contains analgesic and antipyretic properties.

Synthesis
Br Br
Br
HO
O
S
O
OH
Na
+
Br
HO
HO
HO
2-naphthol
Br
CH3Cl base
CH
3
H 1) Mg
H
3
C
O
(+)-naproxen
O
N-alkylglucamine
H
CH
3
OH
2) H3CCHBrCO2MgCl
H
3
C
O
Br
H
3
C O
O
(S)-naproxen, >95% ee
Uses of Aleve
Aleve, or Naproxen, is known as a nonsteroidal anti-inflammatory drug (NSAID) and helps temporarily relieve pain and swelling (inflammation) cause by different situations. It is used to relieve pain in headaches, muscle aches, backaches, tendonitis, dental pain, and menstrual cramps. It can also alleviate pain, swelling, and joint stiffness that is caused by arthritis, bursitis, and gout attacks. These symptoms are all reduced temporarily to help one maintain their daily activities.
Health Effects and Contraindictions of Aleve
Aleve is a blood thinner and could occasionally cause serious bleeding of the stomach or intestines. This condition is rarely serious but should still be treated with caution. This effect could occur spontaneously and occurs more with the elderly.
This pharmaceutical has rarely caused blood clots that have resulted in possibly fatal heart attacks and strokes. With longer treatment of this drug, the patient becomes more at risk for heart problems.
The use of this drug should be stopped immediately if any of the following symptoms occur: black stools, continual stomach or abdominal pain, vomit that looks like coffee grounds, chest pain, shortness of breath, weakness on one side of the body, changes in vision, or slurred speech.

This drug should not be taken if there is pre-existing heart disease, asthma, or the patient is pregnant.