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Related Concept Videos

Oxidation of Phenols to Quinones01:17

Oxidation of Phenols to Quinones

In the presence of oxidizing agents, phenols are oxidized to quinones. Quinones can be easily reduced back to phenols using mild reducing agents. The electron-donating hydroxyl group enhances the reactivity of the aromatic ring, enabling oxidation of the ring even in the absence of an α hydrogen.
o-hydroxy phenols are oxidized to o-quinones and p-hydroxy phenols to p-quinones. Such redox reactions involve the transfer of two electrons and two protons. The reversible redox property is crucial in...
Five-Membered Heterocyclic Aromatic Compounds: Overview01:13

Five-Membered Heterocyclic Aromatic Compounds: Overview

Heterocyclic aromatic compounds are cyclic compounds that are aromatic and have one or more heteroatoms—atoms other than carbon, in the ring. Depending upon the number of atoms present in the ring, they can be either five or six-membered. Examples of five-membered heterocyclic aromatic compounds include pyrrole, furan, thiophene, and imidazole. Pyrrole consists of one nitrogen atom having one lone pair of electrons. Furan and thiophene have one oxygen and one sulfur heteroatom, respectively.
Reactions at the Benzylic Position: Oxidation and Reduction00:59

Reactions at the Benzylic Position: Oxidation and Reduction

The benzylic position describes the position of a carbon atom attached directly to a benzene ring. Benzene by itself does not undergo oxidation. In contrast, the benzylic carbon is quite reactive in the presence of strong oxidizing agents such as KMnO4 or H2CrO4. Therefore, alkylbenzenes are readily oxidized to benzoic acid, irrespective of the type of alkyl groups.
Benzene to 1,4-Cyclohexadiene: Birch Reduction Mechanism01:18

Benzene to 1,4-Cyclohexadiene: Birch Reduction Mechanism

Birch reduction uses solvated electrons as reducing agents. The reaction converts benzene to 1,4-cyclohexadiene. The reaction proceeds by the transfer of a single electron to the ring to form a benzene radical anion. This anion is highly basic—it abstracts a proton from the alcohol to form a cyclohexadienyl radical. Another single electron transfer gives the cyclohexadienyl anion. A proton transfer from the alcohol forms 1,4-cyclohexadiene. Since this reduction occurs via radical anion...
Radical Oxidation of Allylic and Benzylic Alcohols01:21

Radical Oxidation of Allylic and Benzylic Alcohols

Activated manganese(IV) oxide can selectively oxidize allylic and benzylic alcohols via a radical intermediate mechanism. Primary allylic alcohols are oxidized to aldehydes, while secondary allylic alcohols yield ketones. The redox reaction of potassium permanganate with an Mn(II) salt such as manganese sulfate (under either alkaline or acidic conditions), followed by thorough drying, yields the oxidizing agent: activated MnO2. While MnO2 is insoluble in the solvents used for the reaction, the...
NMR Spectroscopy of Benzene Derivatives01:37

NMR Spectroscopy of Benzene Derivatives

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 constants depend...

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Related Experiment Video

Updated: Jun 1, 2026

Real-time Monitoring of Reactions Performed Using Continuous-flow Processing: The Preparation of 3-Acetylcoumarin as an Example
09:56

Real-time Monitoring of Reactions Performed Using Continuous-flow Processing: The Preparation of 3-Acetylcoumarin as an Example

Published on: November 18, 2015

6-Benzyl-oxycoumarin.

Morina Adfa, Mamoru Koketsu, Masahiro Ebihara

    Acta Crystallographica. Section E, Structure Reports Online
    |May 19, 2011
    PubMed
    Summary

    This study details the crystal structure of 6-benzyloxy-2H-1-benzopyran-2-one. Molecular analysis reveals perpendicular coumarin and benzyl planes, stabilized by π-π stacking and C-H⋯O hydrogen bonds.

    Area of Science:

    • Crystallography
    • Organic Chemistry
    • Molecular Structure

    Background:

    • Coumarin derivatives are prevalent in medicinal chemistry and materials science.
    • Understanding the solid-state structure of coumarins is crucial for predicting their properties and designing new molecules.
    • 6-Benzyloxy-2H-1-benzopyran-2-one is a specific coumarin derivative with potential applications.

    Purpose of the Study:

    • To elucidate the crystal structure of 6-benzyloxy-2H-1-benzopyran-2-one.
    • To analyze the molecular conformation and intermolecular interactions within the crystal lattice.
    • To provide insights into the packing motifs of this coumarin derivative.

    Main Methods:

    • Single-crystal X-ray diffraction was employed to determine the crystal structure.

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    Real-time Monitoring of Reactions Performed Using Continuous-flow Processing: The Preparation of 3-Acetylcoumarin as an Example
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  • Analysis of bond lengths, bond angles, and torsion angles.
  • Investigation of intermolecular interactions, including π-π stacking and hydrogen bonding.

    • Main Results:

    • The crystal structure of 6-benzyloxy-2H-1-benzopyran-2-one (C16H12O3) was successfully determined.
    • The coumarin and benzyl moieties exhibit a near-perpendicular orientation (86.92°).
    • Crystal packing is characterized by π-π stacking between coumarin units (3.618 Å separation) and intermolecular C-H⋯O hydrogen bonds.

    Conclusions:

    • The determined crystal structure provides a detailed understanding of the solid-state arrangement of 6-benzyloxy-2H-1-benzopyran-2-one.
    • The observed perpendicular orientation and specific intermolecular interactions are key features influencing the compound's packing and potential properties.
    • This structural information can guide further research into the synthesis and application of related coumarin derivatives.