Synthesis and Prior Misidentification of 4- tert-Butyl-2,6-dinitrobenzaldehyde

J Org Chem. 2019 Sep 20;84(18):12172-12176. doi: 10.1021/acs.joc.9b01737. Epub 2019 Sep 4.

Abstract

Substituted 2,6-dinitrobenzaldehydes are valuable synthetic precursors and have been prepared by several methods. We report here that one reported synthetic method actually forms the 3,5-dinitro isomer, 4-tert-butyl-3,5-dinitrobenzaldehyde, instead of the claimed 2,6-isomer, 4-tert-butyl-2,6-dinitrobenzaldehyde. Improved syntheses for the large-scale preparation of both compounds and their single-crystal X-ray structures are described.

Publication types

  • Research Support, Non-U.S. Gov't