Solvent-Free Conversion of alpha-Naphthaldehyde to 1-Naphthoic Acid and 1-Naphthalenemethanol: Application of the Cannizzaro Reaction

Esteb, John J.; Gligorich, Keith M.; O'Reilly, Stacy A.; Richter, Jeremy M.

doi:10.1021/ed081p1794

Cited by 13 publications

(8 citation statements)

References 2 publications

(1 reference statement)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Transitioning to more benign or recyclable solvents can therefore potentially yield significant benefits from a sustainability standpoint. Mechanochemical milling − and other neat techniques for alcohol oxidations, , Claisen condensations, amine reductions, Cannizzaro, , Wittig, , Baeyer-Villager and Ullman reactions have been adapted to teaching laboratories in order to demonstrate the possibility of removing solvents from organic transformations. If a solvent is indeed necessary for a particular transformation, popular clean solvents such as water, ionic liquids, or CO 2 have become quite commonplace in the chemical education community. ,,− …”

Section: Assessments Focused On Processsesmentioning

confidence: 99%

“… a See ref . b See ref . c See refs , , , , and . d See ref . e See refs − . f See ref . g See ref . h See refs , , . i See ref . j See refs − . k See refs , , − , and − . l See refs − and . m See ref . n See ref . o See refs and . p See refs , , − , and . q See refs and . …”

Section: Cross-curricular Frameworkmentioning

confidence: 99%

See 1 more Smart Citation

Evaluating Feedstocks, Processes, and Products in the Teaching Laboratory: A Framework for Students To Use Metrics to Design Greener Chemistry Experiments

Silverman

Hudson

2019

J. Chem. Educ.

View full text Add to dashboard Cite

Exciting developments in the field of Green Chemistry spur the continuous innovation of experiments in the teaching laboratory. Beyond learning practical techniques, students can critically assess experiments using relevant metrics to propose further improvements and identify the most important interconnected impacts of these alternative products and processes. Herein we review popular laboratory experiments through the simple framework of feedstocks, processes, and products, offering data-driven methods for student evaluation of experiments used in the teaching laboratory. These evaluations employ techniques from life-cycle assessments and techno-economic analyses leveraging freely available data from online databases and safety data sheets. These methods may be used by students and educators to first assess seemingly distinct facets of a chemical transformation (energy inputs, reagent toxicity, etc.) and then relate these to meaningfully address system-wide improvements (replacing harmful solvents, reducing reagent costs, etc.).

show abstract

Section: Assessments Focused On Processsesmentioning

confidence: 99%

Section: Cross-curricular Frameworkmentioning

confidence: 99%

Evaluating Feedstocks, Processes, and Products in the Teaching Laboratory: A Framework for Students To Use Metrics to Design Greener Chemistry Experiments

Silverman

Hudson

2019

J. Chem. Educ.

View full text Add to dashboard Cite

show abstract

“…the synthesis of heterocycles, [90,91] the Wittig, [92] Claisen, [93] and Cannizzaro reaction, [94] and the oxidation of alcohols, [95] thiols, and amines [96] ), we selected a few examples, which demonstrate the advantages of solvent-free operation. the synthesis of heterocycles, [90,91] the Wittig, [92] Claisen, [93] and Cannizzaro reaction, [94] and the oxidation of alcohols, [95] thiols, and amines [96] ), we selected a few examples, which demonstrate the advantages of solvent-free operation.…”

Section: Organic Synthesismentioning

confidence: 99%

Organic Synthesis without Conventional Solvents

Obst

König

2018

Eur J Org Chem

View full text Add to dashboard Cite

Organic synthesis without an organic solvent is still the exception. In this microreview, we discuss and compare different synthetic methods that proceed in the absence of conventional organic solvents. This includes solvent‐free methods in solids (mechanochemistry and solid‐state photochemistry), and in neat liquids (thermal and photocatalytic), as well as the application of unconventional solvents, such as ionic liquids and deep‐eutectic solvents. The different approaches are briefly introduced and examples illustrate their specific advantages, followed by a critical discussion of their limitations. Some methods have the intrinsic benefits of solvent‐free operation, such as avoiding solubility problems and side‐reactions with the solvent. However, every method has specific advantages and the demand of the synthetic application is crucial for selecting the best technique.

show abstract

“…Recently, an article on the iodination of aryl amines captured our attention, as we believed one of the procedures could be successfully modified for a traditional introductory organic laboratory . In fact, several undergraduate laboratory experiments with solvent-free procedures utilizing a mortar and pestle have been reported for the Cannizzarro reaction, synthesis of chalcones, a Grignard reaction, synthesis of quinones or quinhydrones, oxidation of alcohols, and a Wittig reaction − . In week one, the synthesis of 1-iodo-2-nitrobenzene is achieved by subsequent additions and grindings of 2-nitroaniline, minimal water, para -toluenesulfonic acid monohydrate, sodium nitrite, and potassium iodide in a mortar and pestle.…”

Section: Experimental Overviewmentioning

confidence: 99%

Solvent-Free Synthesis of 2,2′-Dinitrobiphenyl: An Ullmann Coupling in the Introductory Organic Laboratory

Gregor

Goj

2010

J. Chem. Educ.

View full text Add to dashboard Cite

The formation of carbon−carbon bonds is an essential theme throughout organic chemistry. The use of transition-metal catalysts to form carbon−carbon bonds, once relegated to more advanced texts, is now commonly found in introductory organic textbooks. However, commensurate laboratory experiments for first-year organic students are more limited. The following experiment utilizes a copper catalyst to create a biphenyl compound, a classical Ullmann coupling reaction. In the first step, 1-iodo-2-nitrobenzene is synthesized from 2-nitroaniline in a mortar. The 1-iodo-2-nitrobenzene is then converted into 2,2′-dinitrobiphenyl by heating in a test tube in the presence of copper and sand. The separation, purification, and identification of the aromatic compounds illustrate the techniques of thin-layer chromatography, column chromatography, melting point, and 1H NMR spectroscopy. Both reactions utilize several green chemistry principles including synthesis in a solvent-free environment, minimal time at reaction temperature, and purification with limited solvent usage. The brightly colored compounds and less common reaction techniques contrast nicely with the traditional refluxing experiments that produce the ubiquitous white powder.

show abstract

Solvent-Free Conversion of alpha-Naphthaldehyde to 1-Naphthoic Acid and 1-Naphthalenemethanol: Application of the Cannizzaro Reaction

Cited by 13 publications

References 2 publications

Evaluating Feedstocks, Processes, and Products in the Teaching Laboratory: A Framework for Students To Use Metrics to Design Greener Chemistry Experiments

Evaluating Feedstocks, Processes, and Products in the Teaching Laboratory: A Framework for Students To Use Metrics to Design Greener Chemistry Experiments

Organic Synthesis without Conventional Solvents

Solvent-Free Synthesis of 2,2′-Dinitrobiphenyl: An Ullmann Coupling in the Introductory Organic Laboratory

Contact Info

Product

Resources

About