. FOHR1).T h e mobile halogen atom in l-chloro-2:4-dinitrobenzene and other halogenonitrobenzenes can be replaced, by interaction with sodium glycolate or sodium glycerolate, by the p-hydroxyethyl-, OCH,.CH,OH and By-dihydroxypropyl, OCH,.CH~OH.CH,OH group, respectively. Glycol and glycerol are sweet but 2 : 4-dinitrophenyl B-hydroxyethyl ether and 2 : 4-dinitrophenyl Ppdihydroxypropyl ether, obtained frcm them, are bitter and these compounds on partial reduction with sodium distilphide afford 2-amino-4-nitrophenyl P-hydroxyethyl ether, which is twenty times as sweet as cane sugar and 2-amino-4-nitrophrnyl-py-dihydroxypropyl ether, which is thirteen times as sweet as cane sugar. Since 2-amino-4-nitrophenyl ethyl ether is 1,400 times and 2-amino-4-nitro-phenyl n-propyl ether, 5.000 times a s sweet as sugar, the replacement of the ethoxy group by a p-hydroxy-ethoxy group and the replacement of n-propoxyby a dihydroxypropoxy group leads to a very considerable decrease in the intensity of the sweet taste. For the development of the sweet taste, in the compound:; mentioned, a free amino group is necessary, since the corresponding acylated derivatives are tasteless, which is in agreement with the observations made previously wifh I-alkoxy-2-amino-4-nitrob-n~enes 2).2 : 4-Dinitrophenyl ,$-hydroxyethyl ether.A solution of sodium (1.8 g ) , in glycol (30 cm3), is prepared and added slowly in portions to a solution of l-chloro-2 : 4-dinitrobenzene (14 g ) , in glycol (25 cm3), and the mixture is then heated on a boiling water-bath for *an hour, poured out into 500 cm3 water, and, after standing overnight, the precipitate is filtered off and recrystallized from water: yield 15 grams (95 "/o).2 : 4-Dinitrophenyl p-hydroxyethyl ether forms colourless needles, m.p. 1 10'. The substance tastes bitter. The compound had previously been prepared by F a i r b o u r n e and T o m s 3 ) . who used a solution of caustic soda in glycol instead of one of sodium in slycol. In this case the solution also reacts as caustic soda and a considerable quantity of 2 : 4-dinitrophenol is produced as a by-product, with the result that the yield of ether is only 60 %, considerably less than when sodium is used. When 2 : 4-dinitrophenyl p-hydroxyethyl ether is heated for a short time with methylamine in alcoholic solution, the glycol residue is replaced by the methylamino group with the production of 2 : 4-dinitro-N-methylaniline, m.p. 175'.2 : 4-Dinitrophenyl p-hydroxyethyl ether acetate. This compound is prepared by dissolving 2 : 4-dinitrophenyl 1-hydroxyethyl ether (0.5 gm.), in acetic anhydride ( 4 cm3). and then adding a drop of concentrated sulphuric acid. The mixture is heated to the boil, poured out ') Part I of Dissertation, F. G.

Both the chlorine atoms in 1,3‐dichloro‐4,6‐dinitrobenzene can be replaced by the glycol residue by interaction with sodium glycolate dissolved in glycol. 4‐6‐Dinitrophenyl‐1,3‐di‐(β‐hydroxyethyl ether), so obtained, gives powerfully explosive nitrate esters when treated with nitric acid; the structure of these esters has been determined by the method described below.

The chlorine atom In l-chloro-2-cyano-4-nitrobenzene can be replaced by the OCH, . CH,OH and the OCH, . CHOH . CH,OH groups, respectively, by treatment with sodium glycolate and sodium glycerolate. With an anhydrous solution of sodium glycolate in glycol at 150", 1-chloro-4-nitrobenzene gives 4-nitrophenyl p-hydroxyethyl ether. No crystalline compound could be obtained by the interaction of sodium glycolerate and 1-chloro-4-nitrobenzene.The chlorine atom in 1 -chloro-2-cyano-4-nitrobenzene is less reactive than that in I-chloro-2 : 4-dinitrobenzene 2 ) . Nevertheless, the halogen atom can be replaced by the glycol and glycerol residues.2-Cyano-4-nitrophenyl p-hydroxyefhyl ether. A solution of caustic soda (1 gram), in a mixture of water ( 1 cm3), and glycol ( 11 cm3). is added to a solution of l-chloro-2-cyano-4-nitrobenzene (3.6 g ), in glycol ( 15 cm3). A dark red solution is produced, which is heated on the water-bath for a further 3 hours, in which tim the solution becomes ( 100 cm3). when there is* produced a yellow precipitate, which is recrystallised from water to give colourless, slightly bitter, felt-like crystals, m.p. 114', of 2-cyano-4-nitrophenyl p-hydroxyethyl ether. The substance is difficulty soluble in petroleum ether, sparingly in the cold but more soluble in boiling water, sparingly soluble in benzene and readily soluble in alcohol, ether and acetone. yellow and sodium chloride separates. The mixture is t 1 en poured into water Analysis:Found. N = 13.5 %. N = 13.5 %. With alcoholic methylamine solution the compound affords 2-cyano-4-nitro-N-methylaniline, m.p. 187'. which is identical with a preparation of the substance previously made by B a u d e t 3). 2-Cyano-4-nitrophenyl p-hydroxyethyl ether, (0.5 g ) , is dissolved in acetyl chloride, (5 cm3). After standing for half an hour, the mixture is poured into water, when an oil is produced, which crystallises on standing. Colourless needles, m.p. 71'. of the above mentioned acetyl derivative are obtained when the product is recrystallised from a mixture of acetone and ether.