Isobutylphenyl propionic Acid

2-(4-Isobutylphenyl)propionic acid (two four eye-so-BYOO-tuhl-PHEEN-uhl PRO-pi-on-ik AS-id) is a colorless crystalline solid widely used as an analgesic and anti-inflammatory medication. It is most commonly known as ibuprofen, but is also known as 0C-methyl-4-(2-methylpropyl)benzeneacetic acid and 

4-isobutyl- alpha -methylphenylacetic acid. It is also sold under a variety of trade names, including Aches-n-Pain , Advil , Andran , Antagil , Antarene , Excedrin IB , Gen-pril , Ibuprin , Medipren , Midol , Motrin , Nuprin , PediaProfen , Rufen , and Vicoprofen . 

Ibuprofen was developed by researchers at the Boots Company, a British drug manufacturer, in the early 1960s. Those researchers had found that the anti-inflammatory property of aspirin was due to the presence of a carboxylic acid (-COOH) group in the compound. They searched for other carboxylic acids that might have similar properties and, after testing more than 600 compounds, discovered that ibuprofen met that criterion. It was twice as effective as 

2 (4 isobutylphenyl) propionic acid. Red atoms are oxygen white atoms are hydrogen and black atoms are carbon. Gray sticks indicate double bonds. Striped sticks indicate a benzene ring. 

In 1974, Boots licensed the Upjohn Company in the United States to begin making a commercial version of Brufen. Upjohn called its product Motrin and marketed the compound primarily to people with arthritis. It soon became a popular drug with both doctors and patients, who found they were able to control the pain of arthritis with a non-addictive product that was easier on the stomach than aspirin. 

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Analgesic and antipyretic ibuprofen, 2-(p-isobutylphenyl)propionic acid, is converted to its monohydroxyaluminum salt by converting the acid to its sodium salt using dilute caustic, foUowed by concurrent addition of equimolar amounts of aluminum nitrate and sodium bicarbonate (84). This salt can also... 

Chemical Name 0 -methyl-4-(2-methylpropyl)ben2ene acetic acid Common Name 2-(4-isobutylphenyl)propionic acid... 

The malonic acid (9 g) was heated to 210° to 220°C in an oil bath for 20 minutes until decarboxylation had ceased. The propionic acid was cooled and recrystallized from light petroleum (BP 60° to 80°C). Two further recrystallizations from the same solvent gave colorless prisms of 2-(4-isobutylphenyl)propionic acid MP 75° to 77.5°C. (The procedure was reported in U.S. Patent 3,228,831.)... 

Ibuprofen (+) -2- (4-Isobutylphenyl) propionic acid Aromatic alkylation, HF-catalyzed aromatic acetylation, palladium-catlayzed carbonylation, alkene hydration... 

Extraction of 25 different binary mixtures of racemic acids (2-(4-isobutylphenyl)-propionic acid (1), and cis- and trans-chrysanthemic (2)), and various chiral bases with supercritical carbon dioxide permitted the conclusion that molecular chiral differentiation in a supercritical fluid is more efficient than in conventional solvents. In the majority of cases, however, complete separation could not be achieved. In five cases, remarkable partial resolutions were realized (30-75% ee) and resolution was possible on a preparative scale. The pair ds-chrysanthemic acid and (S)-(-i-)-2-(benzylamino)-1-butanol (3) was studied in detail. Pressure, temperature, and time, as well as the molar ratio of base and acid, had a marked influence on the quantity and quality of the products. Increasing pressure or decreasing temperature resulted in higher ee values. (-)-cw-Chrysanthemic acid in 99% ee was obtained from the raffinate in a single extraction step. Multiple extractions produced the (-i-)-cA-acid in 90% ee (see fig. 6.3) (Simandi et al., 1997). 

Others have investigated the influence of the presence of (i-cyclodextrin in the reaction medium on the electrochemical carboxylation of a-bromoethylbenzene and l-(4-isobutylphenyl)ethyl chloride [41], It has been reported that the preparative electrocarboxylahon of the inclusion complex (i-cyclodextrin-l-(4-isobutylphenyl) ethylchloride afforded the S-form of 2-(4-isobutylphenyl) propionic acid (S-ibuprofen) in a high enantiomeric excess (97%). 

Isobutylphenyl)propionic acid Hydroxylamine hydrochloride Ethanol... 

Separately, 72.02 g ethyl 2-(4-isobutylphenyl)-propionate, obtained by the esterification of 2-(4-isobutylphenyl)-propionic acid with ethanol and concentrated H2S04, are solved with 100 ml methanol, this solution is introduced drop by drop into the reaction flask, and stirred and cooled for 5... 

In this paper we present a study of the catalytic asymmetric hydrogenation which leads to commercially feasible processes for the production of (S)-2-(6 -methoxy-2 -naphthyl)propionic acid (naproxen) and (S)-2-(p-isobutylphenyl)propionic acid (S-ibuprofen). 

Ibuprofen (2-[4 -isobutylphenyl]propionic acid) is a well-known analgesic marketed as Motrin, Advil , and other brands. U.S. 3,385,886 (to Boots Drug Co.) describes the preparation of the API and several formulations. Estimate the cost of production of the tablet form. 

Synonyms 2-(4-Isobutylphenyl) propionic acid Advil Bayer Select Dayquil Sinus Dimetapp Sinus Dristan Sinus Excedrin IB Haltran Medi-pren Motrin Midol 200 Nuprin Pamprin IB Profen Rufen... 

Racemic 2-(4 -isobutylphenyl)propionitrile is converted by a strain of Acinetobacter sp. to S-(+)-2-(4 -isobutylphenyl)propionic acid with an optical purity >95% (Yamamoto et al. 1990). 

The original method for making ibuprofen developed by Boots researchers begins with 2-methylpropylbenzene, a compound with a four-carbon methylpropyl group attached to a benzene ring. 2-methylpropybenzene is a readily available product with a molecular structure quite similar to that of ibuprofen. Then, in a series of six steps, various groups of atoms are added, removed, or transposed to produce the 2-(4-isobutylphenyl)propionic acid molecule. 

Isobutylphenyl)propionic Acid Acetic acid Methyl Alcohol Retinol... 

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