The Reaction of p-Nitrotoluene with Benzaldehyde in a Sodium-hexamethylphosphoric Triamide-benzene System

Abstract

A prolonged treatment of p-nitrotoluene and benzaldehyde with a sodium-hexamethylphosphoric triamide (HMPA) -benzene mixture was found to give 1-phenyl-2-(4-nitrophenyl)-ethan-1-ol (1) selectively. It was also found that the yield of (1) is sensitively affected by various factors, such as the temperature, the concentration of HMPA, and the reaction time. It may be concluded from the correlation of the yield of (1) and the conversion ratio of p-nitrotoluene that the formation of (1) results from the nucleophilic attack of the p-nitrobenzyl anion, derived from p-nitrotoluene, on the carbonyl carbon of benzaldehyde. © 1971, The Society of Synthetic Organic Chemistry, Japan. All rights reserved.