IN a 12-l. round-bottom flask fitted with a mechanical stirrer are placed 500 g. of technical b-naphthol dissolved in a warm solution of 140 g. of sodium hydroxide in 6 l. of water. The solution is cooled to 0'0 in an ice-and-salt bath, and 250 g. of powdered technical sodium nitrite is added. Stirring is started and 1100 g. of sulfuric acid (sp. gr. 1.32) are added from a dropping funnel, at such a rate that the whole is added in one to one and a half hours, the temperature being kept at 0'0. During the reaction crushed ice is added from time to time to maintain the temperature at 0'0; about 1 kg. is usually used. After all of the sulfuric acid has been added, the solution should react acid to Congo paper. The mixture is stirred one hour longer at the low temperature and then the nitroso-b-naphthol, which has gradually separated out during the reaction, is filtered with suction and washed thoroughly with water. The product is at first light yellow in color, but after three to four days it gradually changes to a dark brown. The moisture content seems to have some effect on the color. After the product has been air-dried for about four days, the yield is about 665 g.; it melts at 97'0. A sample of this partially dried product, on drying _in vacuo_ over sulfuric acid for twenty hours, loses about 10 per cent of its weight and the melting point is 106'0. By longer drying under ordinary conditions, the melting point of 106'0 is reached. The total yield of dry product is about 595 g. (99 per cent of the theoretical amount). This product is satisfactory for all purposes. It may be obtained in a crystalline condition, however, by recrystallizing from hot ligroin (sp. gr. 0.71-0.72). About 2 g. of nitroso-b-naphthol will dissolve in 15 cc. of boiling ligroin. The product is not very soluble in cold ligroin, so that nearly all is recovered. 2. Notes It is very necessary to keep the temperature near 0'0 while adding the sulfuric acid, or a tarry product will be obtained. Vigorous stirring and the addition of the sulfuric acid at the proper rate are essential for a good product. A large vessel is needed for the reaction, as the nitroso-b-naphthol separates in a finely divided condition and there is some tendency to foam. The final air-dried product is pure except for its moisture content, as is shown by the fact that on drying _in vacuo_ it has a very good melting point. A sample of Kahlbaum's nitroso-b-naphthol melted at 101--105. 3. Other Methods of Preparation