ibuprofen synthesis from benzene

After supplemental stock product was obtained, the remainder of the synthesis yielded 12.1% ibuprofen product.Ibuprofen was successfully synthesized from the starting materials isobutylbenzene and acetic anhydride through a Friedel-Crafts acylation, carbonyl reduction, chloride substitution, and Grignard reaction. It is widely used as an important pain killer in therapeutic field.

The IR spectrum displayed the presence of Csp2-H, Csp3-H, C=O, and C=C frequencies with peaks at 3026, 2954 cm, 1684, and 1605 cm-1, respectively. After cooling to rt, 1 L of CO2 was bubbled through the resulting product, 1-(4-isobutylphenyl) ethylmagnesium chloride, and decanted in a separatory funnel with 10 mL of petroleum ether and 16 mL of 10% HCl. The IR spectrum does not contain the broad O-H peak, indicating a replaced alcohol group.Next, the Grignard reagent, 5, was formed by reacting 4 with magnesium in refluxing ether. The so-called "Green" synthesis of ibuprofen involves 3 stepsIn an acylation reaction, an acyl group (RCO-) is attached to the benzene ring producing a ketone.

The first step utilized anhydrous hydrogen fluoride as both a catalyst and solvent, which was then recycled and reused.
: 68 – 69 °C (75-77 °C lit.3). The product was analyzed by IR and 1H NMR spectroscopy.

A 1.0 mL (5.6 mmol) solution of 1-(4-isobutylphenyl)ethane in 20 mL of 12 M HCl was added to a separatory funnel. Step 4: Titrate the contents of the flask with the NaOH(aq) from the burette until a permanent pink colour appears. It is useful for reducing pain, inflammation, and fever. I review two classic industrial organic syntheses of ibuprofen, the Boots process and the Boots-Hoechst-Celanese … It was first patented in 1961 by the Boots Pure Chemical Company, and was approved as an over-the-counter drug in 1984.1 Since its creation, ibuprofen has been marketed under several brand names such as Advil® and Motrin®.In 1992, the BHC Company developed a new, sustainable synthesis that halved the number of synthetic steps (Scheme 1). The 1H NMR spectrum validated the structure of the product. The synthesis of ibuprofen was accomplished from isobutylbenzene. Four step synthesis of Ibuprofen In this experiment ibuprofen was synthesized in four steps.

The IR spectrum suggests the formation of the carboxylic acid with new peaks at 1706 cm-1 indicating the carbonyl bond and a broad peak ranging from 3300 cm-1 to 2400 cm-1 showing the O-H bond. The so-called "Green" synthesis of ibuprofen involves 3 steps 2. To an oven-dried, 50 mL roundbottom flask, 534 mg (2.71 mmol) of 1-chloro-1-(4- isobutylphenyl)ethane, 20 mL of THF, 1.06 g (43 mmol) of magnesium, and a drop of 1,2-dibromomethane were added. Friedel Crafts alkylation of Benzene with Isobutyl Chloride produces Isobutyl Benzene: C6H6 ╃ (H3C)2CHCH2Cl ≡≡≡≡≡≡≡≡⋑ (H3C)2CHCH2C6H5. Compare the structure of the starting material, 2-methylpropylbenzene, with the desired product of the synthesis reactions, ibuprofen: Therefore the synthesis of ibuprofen must involve substituting 1 hydrogen atom on the benzene ring of the 2-methylpropylbenzene starting material for this chain.

Further reactions: various processes used. 20 mL of 10% HCl were added and the aqueous layer was extracted with petroleum ether (3 × 5 mL).

2. Finally, the observed melting point (68 – 69 °C) is similar to the literature melting point3 (75 – 78 °C) of ibuprofen, indicating the synthesis of impure ibuprofen.Prior to the loss of product in step 2, the overall yield of the synthesis was 1.74%. In this article I examine the total synthesis of ibuprofen from benzene. Additionally, the true brilliance behind the BHC method is the reduced amount of unwanted waste due to the generation of only one molecule of water as the byproduct; this, among other factors, have contributed to a genuinely green synthesis.2In this report, we describe a five-step synthesis of ibuprofen that mimics the industrial BHC synthesis. The synthesis of the drug was from isobutyl benzene and 2-hydroxy propanoic acid. The expected product was confirmed through IR and 1H NMR spectroscopy. The 1H NMR spectrum of 4 does not display the hydroxyl hydrogen at 1.45 ppm, and there was a shift in the benzylic hydrogen peak from 4.81 ppm to 5.09 ppm.

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