Intermediate Stages of the Nitration of Hexamethylbenzene to Dinitroprehnitene

A syrupy substance formed in quantity during the nitration of hexamethylbenzene to dinitroprehnitene has been found to be a complex mixture of varying amounts, depending markedly on the conditions, of 2,3,4,5,6-pentamethylbenzyl nitrate, 5,6-bis(nitrooxymethyl)-1,2,3,4-tetramethylbenzene, nitropentamethylbenzene, 6-nitro-2,3,4,5-tetramethylbenzyl nitrate, 2,3,4,5,6-pentamethylphenylnitromethane, bis (2,3,4,5,6-pentamethylbenzyl) ether, pentamethylbenzaldehyde, and several other unidentified carbonyl compounds, nitrite esters, and aliphatic nitro compounds. On the basis of the products isolated, a possible path by which hexamethylbenzene can be converted into dinitroprehnitene has been suggested.