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Related Concept Videos

Hydrolysis of Chlorobenzene to Phenol: Dow Process01:10

Hydrolysis of Chlorobenzene to Phenol: Dow Process

Simple aryl halides do not react with nucleophiles under normal conditions. However, the reaction can proceed under drastic conditions involving high temperatures and high pressure to give the substituted products. For example, chlorobenzene is converted to phenol using aqueous sodium hydroxide at 350 °C under high pressure by the Dow process. The reaction follows an elimination-addition mechanism involving a benzyne intermediate. Here, the chloride ion is eliminated to generate the benzyne...
Reactions at the Benzylic Position: Halogenation01:11

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Benzylic halogenation takes place under conditions that favor radical reactions such as heat, light, or a free radical initiator like peroxide.
Nucleophilic Aromatic Substitution: Elimination–Addition01:11

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Simple aryl halides do not react with nucleophiles. However, nucleophilic aromatic substitutions can be forced under certain conditions, such as high temperatures or strong bases. The mechanism of substitution under such conditions involves the highly unstable and reactive benzyne intermediate. Benzyne contains equivalent carbon centers at both ends of the triple bond, each of which is equally susceptible to nucleophilic attack. This 50–50 distribution of products is confirmed through isotopic...
Reactions at the Benzylic Position: Oxidation and Reduction00:59

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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.
Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration02:34

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Hydroboration-Oxidation of Alkenes03:08

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In addition to the oxymercuration–demercuration method, which converts the alkenes to alcohols with Markovnikov orientation, a complementary hydroboration-oxidation method yields the anti-Markovnikov product. The hydroboration reaction, discovered in 1959 by H.C. Brown, involves the addition of a B–H bond of borane to an alkene giving an organoborane intermediate. The oxidation of this intermediate with basic hydrogen peroxide forms an alcohol.

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Propyl 4-amino-benzoate.

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Dicarbonyl-1κ<sup>2</sup> <i>C</i>-μ-chlorido-2:3κ<sup>2</sup> <i>Cl</i>:<i>Cl</i>-penta-chlorido-2κ<sup>2</sup> <i>Cl</i>,3κ<sup>3</sup> <i>Cl</i>-[1(η<sup>6</sup>)-toluene]digallium(III)ruthenium(I)(<i>Ru</i>-<i>Ga</i>).

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<i>trans</i>-Di-aqua-tetra-kis-(tetra-hydro-furan-κ<i>O</i>)iron(II) μ-carbonyl-tetra-deca-carbonyl-tetra-chlorido-μ-di-methyl-silanediolato-tetra-galliumtetra-iron(7 <i>Ga</i>-<i>Fe</i>)(<i>Fe</i>-<i>Fe</i>) tetra-hydro-furan tetrasolvate.

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Updated: Jul 7, 2026

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
08:43

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Published on: January 19, 2016

Ethyl 3-hy-droxy-benzoate.

Alexander J Gutzwiller1, Grace E Addison1, Christine K F Hermann1

  • 1PO Box 6949, Radford University, Radford, Virginia 24142, USA.

Iucrdata
|July 6, 2026
PubMed
Summary

This study details the crystal structure of ethyl 3-hydroxybenzoate, revealing two independent molecules. Hydrogen bonding forms planar chains, influencing molecular orientation and crystal packing.

Area of Science:

  • Crystallography
  • Organic Chemistry
  • Molecular Structure

Background:

  • Ethyl 3-hydroxybenzoate is an organic compound with potential applications in various chemical syntheses.
  • Understanding the crystalline structure of organic molecules is crucial for predicting their physical and chemical properties.
  • Previous studies may have investigated related benzoate esters, but specific crystallographic data for ethyl 3-hydroxybenzoate might be limited.

Purpose of the Study:

  • To determine and describe the crystal structure of ethyl 3-hydroxybenzoate.
  • To analyze the molecular geometry, including planarity and torsion angles, of ethyl 3-hydroxybenzoate.
  • To investigate intermolecular interactions, such as hydrogen bonding, within the crystal lattice.

Main Methods:

  • Single-crystal X-ray diffraction was employed to collect diffraction data.
Keywords:
crystal structurehydrogen bonding

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  • The crystal structure was solved and refined using standard crystallographic software.
  • Analysis of bond lengths, bond angles, torsion angles, and intermolecular contacts was performed.

    • Main Results:

    • The crystal structure of ethyl 3-hydroxybenzoate (C9H10O3) was determined, revealing two independent molecules in the asymmetric unit.
    • Each molecule exhibits approximate planarity, with the ethyl group oriented away from the carbonyl oxygen.
    • Hydroxyl-O-H⋯O(carbonyl) hydrogen bonding was observed, forming nearly planar chains along the [100] direction.

    Conclusions:

    • The crystal packing of ethyl 3-hydroxybenzoate is governed by intermolecular hydrogen bonding, leading to the formation of extended chains.
    • The observed planarity and specific torsion angles provide insights into the conformational preferences of the molecule in the solid state.
    • This detailed crystallographic analysis contributes to the understanding of structure-property relationships in benzoate esters.