Nitro-2-naphthoxyacetic Acid

A solution of 100 g. (0.49 mole) of /J-naphthoxyacetic acid (p. 209) in 600 ml. of glacial acetic acid is cooled and stirred during the cautious addition of 70 ml. of concentrated nitric acid. The mixture is allowed to stand for 2 hours, and the precipitated nitro compound is collected by filtration and washed with acetic acid. The product is recrystallized from acetic acid to give an 80% yield of l-nitro-2-naphthoxyacetic acid which melts at 188-189°. [Pg.229]

A solution of 139 g. (1.0 mole) of m-nitrophenol [Org. Syntheses Coll. Vol. 1, 404 (1941)] in 250 ml. of 20% aqueous sodium hydroxide solution is heated to reflux. A total of 215 g. (1.07 moles) of ethyl p-toluenesulfonate is added in 50-g. portions at intervals of 10-15 [Pg.229]

A mixture of 100 g. (0.75 mole) of o-nitroaniline and 500 ml. of a 1 1 mixture of water and concentrated hydrochloric acid is diazotized by the careful addition of an aqueous solution of 55 g. (0.80 mole) of sodium nitrite at 10°. The mixture is stirred for 15 minutes after the completion of the addition, the solution is filtered, and the filtrate is added slowly with agitation and cooling below 0° to 550 ml. of 25 sodium hydroxide solution. The resulting solution is added to a solution of 135 g. of sodium arsenite in 1250 ml. of water, and the mixture is heated to 60-70° for 2 hours, care being taken not to overheat it. This is followed by acidification with acetic acid, treatment with activated carbon, and the addition of hydrochloric acid until the mixture is strongly acid to Congo red. Cooling the mixture in ice precipitates 110 g. (61%) of yellow powder, which after one recrystallization from water melts at 235-240° (dec.). [Pg.231]

Muller, Montigel, and Reichstein, Helv. Chim. Acta, 20, 1472 (1937). [Pg.232]

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