Nitroso-b-naphthol has been made by the action of hydroxylamine hydrochloride on b-naphtho-quinone-chlorimide;[1] by the action of sulfuric acid upon a solution of potassium or sodium nitrite and the sodium salt of b-naphthol;[2] by the action of sodium nitrite upon an alcoholic solution of zinc chloride and b-naphthol;[3] by the action of sodium nitrite upon b-naphthol suspended in zinc sulfate solution;[4] by the action of nitrous acid on b-dinaphthol methane;[5] and by the action of nitrosyl sulfate upon the sodium salt of b-naphthol.[6] [1] Ber. 27, 241 (1894). [2] Ber. 8, 1026 (1875); 27, 3076 (1894); J. Chem. Soc. 45, 295 (1884). [3] Ber. 18, 705 (1885). [4] D. R. P. 25,469; Frdl. 1, 335 (1883). [5] Ber. 33, 806 (1900). [6] J Chem. Soc. 32, 47 (1877); Ann. 189, 146 (1877). XVII PHENYLACETIC ACID C6H5CH2CN + 2H2O + H2SO4--> C6H5CH2CO2H + NH4HSO4 Prepared by ROGER ADAMS and A. F. THAL. Checked by O. KAMM and A. O. MATTHEWS. 1. Procedure IN a 5-l. round-bottom flask, fitted with a mechanical stirrer and reflux condenser, are mixed 1150 cc. of water, 840 cc. of commercial sulfuric acid and 700 g. of benzyl cyanide (preparation III, p. 9). The mixture is heated under a reflux condenser and stirred for three hours, cooled slightly and then poured into 2 l. of cold water. The mixture should be stirred so that a solid cake is not formed; the phenylacetic acid is then filtered off. This crude material should be melted under water and washed by decantation several times with hot water. These washings, on cooling, deposit a small amount of phenylacetic acid which is filtered off and added to the main portion of material. The last of the hot water is poured off from the material while it is still molten and it is then transferred to a 2-l. Claisen distilling flask and distilled _in vacuo_. A small amount of water comes over first and is rejected; about 20 cc., containing an appreciable amount of benzyl cyanide, then distils. This fraction is used in the next run. The distillate boiling 176-189'0/50 mm. is collected separately and solidifies on standing. It is practically pure phenylacetic acid, m. p. 76-76.5'0; it amounts to 630 g. (77.5 per cent of the theoretical amount). As the fraction which is returned to the second run of material contains a considerable portion of phenylacetic acid, the yield actually amounts to at least 80 per cent. For the preparation of small quantities of phenylacetic acid, it is convenient to use the modified method given in the Notes. 2. Notes