DE2165998

1363870 Substituted 3 - (4 - hydroxynaphthyl) - naphthalide - 1,8: 1 - hydroxy - 2- naphthoic acid derivatives POLAROID CORP 28 May 1971 [5 June 1970 4 Jan 1971 (3)] 1008/74 Divided out of 1363866 Heading C2C [Also in Division C4] 3 - Hydroxy - 3 - (31 - carbomethoxy - 41- hydroxynaphthyl) - naphthalide - 1,8 is prepared by adding anhydrous aluminium chloride to 1 - hydroxy - 2 - methylnaphthoate dissolved in dry 1,1,2,2-tetrachloroethane, adding nitrobenzene, adding this solution dropwise to 3,3 - dichloronaphthalide in 1,1,2,2 - tetrachloroethane, adding excess ice followed by concentrated hydrochloric acid, distilling the organic solvents with steam using a distillation head, taking up the solid in hot glacial acetic aicd, filtering insoluble material and allowing the desired product to crystallize. 1-Hydroxy-2- methyl naphthoate is prepared by adding chilled anhydrous methanol to 1-hydroxy-2-naphthoyl chloride. 1-Hydroxy-2-naphthoyl chloride is prepared by adding thionyl chloride in dry N,N-dimethylformamide to dry 1-hydroxy-2- naphthoic acid suspended in dry benzene. 3 - [H] - 3 - (21 - n - Propylsulphamoyl - 4- hydroxy - naphthyl - ) - naphthalide - 1,8 is prepared by dissolving 2-n-propylsulphamoyl-1- naphthol and naphthaldehydic acid in acetic acid, adding p-toluenesulphonic acid in acetic acid, refluxing, pouring the mixture into an equal volume of cold water and recrystallizing the product. 2-n-Propylsulphamoyl-1-naphthol is prepared by adding a mixture of diisopropylethylamine and n-propylamine to 1-carbomethoxy - naphthalene - 2 - sulphonyl chloride in chloroform at 50-60‹ C., heating, cooling, acidifying and evaporating the chloroform. 3 - Chloro - 3 - (31 - carbomethoxy - 41 - hydroxynaphthyl) - naphthalide - 1,8 is prepared by adding thionyl chloride and then dry N,N- dimethylformamide to 3-hydroxy-3-(31-carbomethoxy - 41 - hydroxynaphthyl) - naphthalide- 1,8 suspended in dry benzene. 1,6-Dihydroxy-2- naphthoic acid is prepared by refluxing a mixture containing 1 - hydroxy - 6 - octadecyloxy - 2- naphthoic acid prepared by adding sodium methoxide to a solution of 1,6-dihydroxynaphthalene in dry N,N-dimethylformamide saturated with dry carbon dioxide gas, cooling, acidifying and pouring onto ice. 1-Hydroxy-6- octadecyloxy-2-naphthoic acid is prepared by adding potassium t-butoxide to a slurry of 1,6-dihydroxy-2-naphthoic acid in dry isopropyl alcohol under nitrogen, refluxing, adding octadecyl bromide, refluxing, cooling, acidifying and filte