Synthesis of Ibuprofen in the Introductory Organic Laboratory

Kjonaas, Richard A.; Williams, P.; Counce, David A.; Crawley, Lindsey R.

doi:10.1021/ed100892p

Cited by 26 publications

(20 citation statements)

References 19 publications

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“…1-Chloro-(4isobutylphenyl)ethane (1) was synthesised following that in the literature. 42 N-Methyl-N-propylpiperidinium bis(tri-uoromethanesulfonyl)imide (PP13 TFSI, purity 99.5%, H 2 O # 0.05%), 1-methyl-1-ethylimidazolium bis(tri-uoromethanesulfonyl)imide (EMIM TFSI, purity 99%, H 2 O # 0.2%) were acquired from Solvionic, and were dried under vacuum using activated molecular sieves for 24 h to make sure that the amount of water was always less than H 2 O # 0.001% (Scheme 2).…”

Section: Methodsmentioning

confidence: 99%

Electrocarboxylation of 1-chloro-(4-isobutylphenyl)ethane with a silver cathode in ionic liquids: an environmentally benign and efficient way to synthesize Ibuprofen

2019

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Section: Methodsmentioning

confidence: 99%

Electrocarboxylation of 1-chloro-(4-isobutylphenyl)ethane with a silver cathode in ionic liquids: an environmentally benign and efficient way to synthesize Ibuprofen

2019

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“…The synthetic procedure for this step was a modification of the synthesis previously published by Kjonaas et al [14]. A solution of p-isobutylacetophenone (1.20 mL), methanol (3.00 mL), and sodium borohydride (0.2509 g) was mixed in a separatory funnel and allowed to sit for 10 min.…”

Section: -(4-isobutylphenyl)ethanol Synthesismentioning

confidence: 99%

“…The synthetic procedure for this step was a modification of the synthesis previously published by Kjonaas et al [14]. A solution of 1-(4-isobutylphenyl)ethanol (1.10 mL) was placed into a separatory funnel and mixed with 12.0 M HCl (10.0 mL) for a period of 5 min.…”

Section: -Chloro-1-(4-isobutylphenyl)ethane Synthesismentioning

confidence: 99%

“…The synthetic procedure for this step was a modification of the synthesis previously published by Kjonaas et al [14]. A solution of 1-chloro-1-(4-isobutylphenyl)ethane (0.25 mL), magnesium (0.507 g), THF (10.00 mL) and 1,2-dibromoethane (4 drops) was placed in a dry 50-mL round bottom flask that had been painted black using VHT ® Flame Proof paint.…”

Section: Ibuprofen Synthesis Via Grignard Reaction Using Solar Heat Smentioning

confidence: 99%

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Progress towards a more sustainable synthetic pathway to ibuprofen through the use of solar heating

Agee

Mullins

Swartling

2016

Sustain Chem Process

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The ACS Green Chemistry Institute Pharmaceutical Roundtable was formed in 2005 to encourage the incorporation of green chemistry techniques into the synthetic pathways of pharmaceuticals. Through this initiative, synthetic pathways of several pharmaceuticals have been altered to adapt more environmentally friendly procedures. The amount of electricity required to complete chemical reactions have become an environmental concern due to depleting fossil fuels. A technique was recently developed in which satellite dishes were repurposed as solar reflectors capable of providing a heat source through solar irradiation. The ability to use the solar reflector as the sole heat source for synthetic reactions has been analyzed for the commercially important pharmaceutical, ibuprofen. Ibuprofen synthesis also incorporates chemicals that are not particularly friendly to the environment. The exchange of these chemicals with more environmentally friendly substitutes has been analyzed. The goal of this study is to incorporate a solar energy heat source to develop an alternative energy, more environmentally friendly pathway to ibuprofen.

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“…The two enantiomers have different biological behavior, the S(+)-enantiomer being the eutomer, but R(-)-ibuprofen is partially converted to form S(+) in biological environment [1,2]. There were many attempts to isolate the eutomer from racemate or to find a specific chemical synthesis of single enantiomer.…”

Section: Introductionmentioning

confidence: 99%

Research Article. The Influence of Some Parameters on Chiral Separation of Ibuprofen by High-Performance Liquid Chromatography and Capillary Electrophoresis

Balint

Cârje

Muntean

et al. 2017

Acta Medica Marisiensis

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Objective: The aim of the study was to compare the influence of mobile phase composition and temperature on chiral separation of racemic ibuprofen by capillary electrophoresis and high performance liquid chromatography with UV detection. Materials and methods: Racemic ibuprofen was analysed on a chiral OVM column with an HPLC system 1100 Agilent Technologies, under isocratic elution, by using potassium dihydrogen phosphate 20 mM and ethanol in mobile phase. The flow rate was set at 1 mL/min, UV detector at 220 nm and different column temperatures were tested. For electrophoresis separation an Agilent CE G1600AX Capillary Electrophoresis System system, with UV detection, was used. The electrophoresis analysis was performed at different pH values and temperatures, with phosphate buffer 25 mM and methyl-β-cyclodextrin as chiral selector. Results: The chromatograhic analysis reveals a high influence of mobile phase pH on ibuprofen enantiomers separation. An elution with a mixture of potassium dihydrogen phosphate 20 mM pH=3 and ethanol, at 25ºC, allowed enantiomers separation with good resolution in less than 8 min. Conclusions: The proposed HPLC method proved suitable for the separation of ibuprofen enantiomers with a good resolution, but the capillary electrophoresis tested parameters did not allow chiral discrimination.

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Synthesis of Ibuprofen in the Introductory Organic Laboratory

Cited by 26 publications

References 19 publications

Electrocarboxylation of 1-chloro-(4-isobutylphenyl)ethane with a silver cathode in ionic liquids: an environmentally benign and efficient way to synthesize Ibuprofen

Electrocarboxylation of 1-chloro-(4-isobutylphenyl)ethane with a silver cathode in ionic liquids: an environmentally benign and efficient way to synthesize Ibuprofen

Progress towards a more sustainable synthetic pathway to ibuprofen through the use of solar heating

Research Article. The Influence of Some Parameters on Chiral Separation of Ibuprofen by High-Performance Liquid Chromatography and Capillary Electrophoresis

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