Sulfuric Acid-Promoted Oxidation of Benzylic Alcohols to Aromatic Aldehydes in Dimethyl Sulfoxide: An Efficient Metal-Free Oxidation Approach

Ehsan Sheikhi; Mehdi Adib; Morteza Akherati Karajabad; Seyed Jamal Addin Gohari

doi:10.1055/s-0037-1609149

Synlett, Table of Contents

Synlett 2018; 29(07): 974-978
DOI: 10.1055/s-0037-1609149

letter

Sulfuric Acid-Promoted Oxidation of Benzylic Alcohols to Aromatic Aldehydes in Dimethyl Sulfoxide: An Efficient Metal-Free Oxidation Approach

Ehsan Sheikhi*

^aSchool of Chemistry, College of Science, University of Tehran, PO Box 14155-6455, Tehran, Iran Email: ehsan.sheikhi@gmail.com Email: madib@khayam.ut.ac.ir

,

Mehdi Adib*

^aSchool of Chemistry, College of Science, University of Tehran, PO Box 14155-6455, Tehran, Iran Email: ehsan.sheikhi@gmail.com Email: madib@khayam.ut.ac.ir

,

Morteza Akherati Karajabad

^aSchool of Chemistry, College of Science, University of Tehran, PO Box 14155-6455, Tehran, Iran Email: ehsan.sheikhi@gmail.com Email: madib@khayam.ut.ac.ir

,

Seyed Jamal Addin Gohari

^bDepartment of Chemistry, Imam Hossein University, Tehran, Iran

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Abstract

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Abstract

An efficient metal-free oxidation of benzylic alcohols to aromatic aldehydes is described. Heating a solution of the benzylic alcohol in DMSO in the presence of H₂SO₄ afforded the corresponding aldehyde in excellent yield. This oxidation reaction, which proceeds with a short reaction time and no side products, is akin to the Pfitzner–Moffatt oxidation, but without the need for N,N′-dicyclohexylcarbodiimide.

Key words

benzylic alcohols - aromatic aldehydes - sulfuric acid - dimethyl sulfoxide - oxidation

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References

References and Notes

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22 Aldehydes 2a–n; General Procedures Protocol A: A mixture of the benzylic alcohol 1 (1 mmol) and 98% H₂SO₄ (1 mmol) in DMSO (3 mL) was stirred for the appropriate time under reflux conditions. The mixture was then cooled to r.t., and brine (4 mL) was added. The organic phase was extracted with CH₂Cl₂ (6 mL), and the organic layer was dried (Na₂SO₄), filtered, and concentrated under reduced pressure. In all cases, the reaction products were obtained with high purity, and did not require further purification by distillation or column chromatography. Protocol B: A mixture of benzylic alcohol (1 mmol) and 98% H₂SO₄ (0.5 mmol) in DMSO (3 mL) was stirred for the appropriate reaction time under reflux conditions. The reaction mixture was then worked up as described in Protocol A.