Nitric Acid → 1,1,2,3,3,5-Hexamethyl-6-nitro-2,3-dihydro-1H-indene

Participants

Reaction Conditions

Reaction Steps

To a 500 ml reaction vessel equipped with stirrer, thermometer, reflux condensor, addition funnel and cooling bath is placed 51 grams of 1,1,2,3,3,6-hexamethyl indane having the structure: ##STR40## (51 grams) in admixture with 100 grams of acetic acid. The resulting mixture is cooled to 10° C. Over a period of 0.5 hours, 40 grams of fuming nitric acid is added to the reaction mass, while maintaining the reaction mass at 10° C. Over a period of 10 minutes, 10 grams of concentrated sulfuric acid is then added to the reaction mass. The reaction mass is then heated to 25° C. and maintained at 25° C. for a period of 3.5 hours. At the end of the 3.5 hour period, the reaction mass is quenched with ice water (500 ml) and crystals are formed. The crystals are then re-crystallized from water. The melting point of the resulting crystals is 115.7° C. NMR, IR and mass spectral anaylses yield the information that the compound has the structure: ##STR41##

Provenance & Evidence