Barnes and Hickinbottom. 953 196. 4 -Nitro-2,6ditbut ylp hen01 and its Thermal Decomposition.By T. J. BARNES and W. J. HICKINBOTTOM.ZJ6-Di-t-buty1phenol can be nitrated a t position 4 in acetic acid solution by nitric acid. Other products are 3,3',5,5'-tetra-t-buty1-4,4'-diphenoquinone and 4,4'-dihydroxy-3,3',5,5'-tetra-t-butylbiphenyl with some 2,6-dit-bu tyl-1,4-benzoquinone.When heated, the nitrophenol decomposes into nitric oxide, 3,3',5,5'tetra-t-buty1-4,4'-diphenoquinoneJ 2,6-di-t-butyl-1,4-benzoquinone 4-oximeJ and water.Other reactions resulting in the elimination of the nitro-group of the nitrophenol are reported.PREVIOUS attempts to nitrate 2,6-di-t-butylphenol (I) resulted either in oxidation to 3,3',5,5'-tetra-t-butyl-4,4'-diphenoquinone (111) or in the expulsion of a t-butyl-group with the formation of 2,4-dinitr0-6-t-butyIphenol.~ It is now shown that, by attention to detail, mononitration of the phenol can be achieved; * the yield of 4-nitro-2,6-di-tbutylphenol (11) is about 30%, the remainder of the product being 3,3',5,5'-tetra-t-butyl-4,4'-diphenoquinone (111) and 4,4'-dihydroxy-3,3',5,5'-tetra-t-butylbiphenyl with some 2,6-di-t-butyl-l,4-benzoquinone.The reactions of the nitrophenol (11) are unusual: it gives the Liebermann nitrosotest; it decomposes on being heated into the diphenoquinone (111), nitric oxide, and water ; it is hydrolysed by sulphuric acid t o 2,6-di-t-butyl-l,4-benzoquinone and its * After this paper had been completed we learnt that Dr. K. U. Ingold has also prepared 4-nitro-2,6-di-t-butylphenol by nitration of 2.6-di-t-butylphenol, and that he has hydrogenated it to the aminophenol.