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¹H NMR: Complex Splitting

¹H NMR: Complex Splitting

A proton M that is coupled to a proton X results in doublet signals for M. However, NMR-active nuclei can be simultaneously coupled to more than one nonequivalent nucleus. When M is coupled to a second proton A, such as in styrene oxide, each peak in the doublet is split into another doublet.
Splitting diagrams or splitting tree diagrams are routinely used to depict such complex couplings. While drawing splitting diagrams, the splitting with the larger coupling constant is usually applied...

Preparation of 1° Amines: Gabriel Synthesis

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Direct alkylation is not a suitable method for synthesizing amines because it produces polyalkylated products. Gabriel synthesis is the most preferred method to exclusively make primary amines. The method uses phthalimide, which contains a protected form of nitrogen that participates in alkylation only once to predominantly give primary amines.
Strong bases like NaOH or KOH deprotonate the phthalimide to form the corresponding anion, which acts as a nucleophile. Further, the anion attacks an...

Aldehydes and Ketones with HCN: Cyanohydrin Formation Overview

Aldehydes and Ketones with HCN: Cyanohydrin Formation Overview

Cyanohydrins are compounds that contain –CN and –OH groups on the same carbon atom. They are formed by the nucleophilic addition of the cyanide ions to the carbonyl group. Cyanide ions are highly basic and nucleophilic and can be generated from HCN under aqueous conditions. However, since HCN is a weak acid, the number of cyanide ions generated is very small. Hence, a small amount of base or KCN/NaCN is added to HCN to increase the concentration of the cyanide ions in the reaction...

NMR Spectroscopy of Benzene Derivatives

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Simple unsubstituted benzene has six aromatic protons, all chemically equivalent. Therefore, benzene exhibits only a singlet peak at δ 7.3 ppm in the 1H NMR spectrum. The observed shift is far downfield because the aromatic ring current strongly deshields the protons. Any substitution on the benzene ring makes the aromatic protons nonequivalent, and the protons split each other. The peak is, therefore, no longer a singlet and the splitting pattern and their associated coupling...

Prochirality

Prochirality

The concept of prochirality leads to the nomenclature of the individual faces of a molecule and plays a crucial role in the enantioselective reaction. It is a concept where two or more achiral molecules react to produce chiral products. A typical process is the reaction of an achiral ketone to generate a chiral alcohol. Here, the achiral reactant reacts with an achiral reducing agent, sodium borohydride, to generate an equimolar mixture of the chiral enantiomers of the product. For example, an...

¹H NMR Chemical Shift Equivalence: Enantiotopic and Diastereotopic Protons

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Replacing each alpha-hydrogen in chloroethane by bromine (or a different functional group) yields a pair of enantiomers. Such protons are called prochiral or enantiotopic and are related by a mirror plane. Enantiotopic protons are chemically equivalent in an achiral environment. Because most proton NMR spectra are recorded using achiral solvents, enantiotopic hydrogens yield a single signal.
In chiral compounds such as 2-butanol, replacing the methylene hydrogens at C3 produces a pair of...

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Related Experiment Video

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Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy

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Multigram Synthesis of Pure HMF and BHMF.

Giacomo Trapasso¹, Giovanna Mazzi¹, Beatriz Chícharo¹

¹Department of Environmental Sciences Informatics and Statistics, Ca' Foscari University of Venice, Via Torino, 155, 30170 Mestre, Venezia, Italy.

Organic Process Research & Development

|October 31, 2022

Summary

This study presents an efficient method for producing 5-hydroxymethylfurfural (HMF), a key bio-based chemical, from d-fructose. The developed process offers a greener and potentially more cost-effective route for industrial applications.

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Published on: October 8, 2016

Area of Science:

Green Chemistry
Biomass Conversion
Platform Chemicals

Background:

5-Hydroxymethylfurfural (HMF) is a versatile bio-based platform chemical with significant industrial potential.
Current HMF synthesis methods face challenges in cost-effectiveness and industrial scalability.

Purpose of the Study:

To develop a multigram-scale, cost-effective, and sustainable procedure for HMF synthesis.
To evaluate the environmental impact and efficiency of the proposed method.

Main Methods:

Reaction of d-fructose with an acidic resin (Purolite CT275DR) in a dimethyl carbonate (DMC)/tetraethyl ammonium bromide (TEAB) biphasic system.
Utilized an autoclave for reactions at 110 °C for 2 hours.
Developed a custom purification procedure for crystalline HMF and subsequent reduction of residual oil to bis(hydroxymethyl)furan (BHMF).

Main Results:

Achieved an overall HMF yield of 70% from up to 40 grams of d-fructose.
Obtained approximately 50% pure crystalline HMF product.
Successfully reduced the HMF-rich oil to bis(hydroxymethyl)furan (BHMF).

Conclusions:

The developed procedure offers a promising route for scalable and sustainable HMF production.
The method demonstrates improved green metrics and Ecoscale evaluation compared to existing technologies.
This work contributes to the advancement of bio-based chemical manufacturing.