Synlett 2018; 29(07): 974-978
DOI: 10.1055/s-0037-1609149
letter
© Georg Thieme Verlag Stuttgart · New York

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

Ehsan Sheikhi*
a   School 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*
a   School 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
a   School 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
b   Department of Chemistry, Imam Hossein University, Tehran, Iran
› Author Affiliations
This research was supported by the Research Council of University of Tehran.
Further Information

Publication History

Received: 17 October 2017

Accepted after revision: 18 December 2017

Publication Date:
29 January 2018 (online)


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.