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Preparation of Diols and Pinacol Rearrangement01:57

Preparation of Diols and Pinacol Rearrangement

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Compounds bearing two hydroxyl groups are known as diols. When the hydroxyl groups are located on adjacent carbon atoms, the diols are called vicinal diols or glycols. Under acidic conditions, vicinal diols undergo a specific reaction called pinacol rearrangement.
The reaction begins with transferring a proton from the acid catalyst to one of the hydroxyl groups, producing an oxonium ion.
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Vicinal Diols via Reductive Coupling of Aldehydes or Ketones: Pinacol Coupling Overview01:27

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Wilhelm Rudolph Fittig discovered the pinacol coupling reaction in 1859. It is a radical dimerization reaction and involves the reductive coupling of aldehydes or ketones in the presence of hydrocarbon solvent to yield vicinal diols.
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Electrocyclic reactions are reversible reactions. They involve an intramolecular cyclization or ring-opening of a conjugated polyene. Shown below are two examples of electrocyclic reactions. In the first reaction, the formation of the cyclic product is favored. In contrast, in the second reaction, ring-opening is favored due to the high ring strain associated with cyclobutene formation.
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Photochemical Electrocyclic Reactions: Stereochemistry01:26

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The absorption of UV–visible light by conjugated systems causes the promotion of an electron from the ground state to the excited state. Consequently, photochemical electrocyclic reactions proceed via the excited-state HOMO rather than the ground-state HOMO. Since the ground- and excited-state HOMOs have different symmetries, the stereochemical outcome of electrocyclic reactions depends on the mode of activation; i.e., thermal or photochemical.
Selection Rules: Photochemical Activation
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Benzaldehyde, like formaldehyde, lacks an α hydrogen and cannot enolize to form an enolate. Hence, the reaction of benzaldehyde with a ketone in the presence of an aqueous base forms a single crossed product. This reaction is referred to as Claisen–Schmidt condensation.
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Aldehydes and ketones are prepared from alcohols, alkenes, and alkynes via different reaction pathways. Alcohols are the most commonly used substrates for synthesizing aldehydes and ketones. The conversion of alcohol to aldehyde, which involves the oxidation process, depends on the class of the alcohol used and the strength of the oxidizing agent. For instance, primary alcohol will form an aldehyde when treated with a weak oxidizing agent; however, it gets over-oxidized to a carboxylic acid in...
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Biosynthesis of a Flavonol from a Flavanone by Establishing a One-pot Bienzymatic Cascade
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A Concise Route to Keto-Bridged Polyphenols by Photo-Fries Rearrangement in Flow.

Xin-Jie Lin1, Chien-Lung Wang2, Chi-How Peng2

  • 1Department of Applied Chemistry, National Yang Ming Chiao Tung University, No. 1001 University Road, Hsinchu, 30010, Taiwan.

Chemistry, an Asian Journal
|April 15, 2024
PubMed
Summary

A novel synthesis for bis(2-hydroxy-3,5-di-t-butylphenyl)methanone and derivatives was developed. This efficient, protecting-group-free method uses a combined esterification/photo-Fries rearrangement for scalable polyphenol production.

Keywords:
hydroxybenzophenoneoxygen donor ligandphenolphoto-Fries rearrangementphotoflow synthesis

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Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry
  • Polymer Science

Background:

  • Bis(2-hydroxy-3,5-di-t-butylphenyl)methanone derivatives are valuable polyphenols.
  • Existing synthetic routes can be complex and inefficient.

Purpose of the Study:

  • To develop a new, efficient synthetic route to bis(2-hydroxy-3,5-di-t-butylphenyl)methanone and its derivatives.
  • To establish a modular and scalable preparation method for keto-bridged polyphenols.

Main Methods:

  • A combined esterification and photo-Fries rearrangement approach.
  • Protecting-group-free synthesis.
  • Continuous-flow mode for scalable production.

Main Results:

  • Successfully synthesized bis(2-hydroxy-3,5-di-t-butylphenyl)methanone and its derivatives.
  • The process is highly atom- and step-economic.
  • Scalable production was achieved in continuous-flow.

Conclusions:

  • The novel synthetic route offers an efficient and modular preparation of keto-bridged polyphenols.
  • The protecting-group-free and continuous-flow process is suitable for industrial applications.