[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([OH:12])=[CH:4][C:3]=1[C:13]([OH:15])=[O:14].[OH-].[Na+].[CH2:18](Br)[C:19]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:20]>CN(C=O)C>[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([O:12][CH2:18][C:19](=[O:20])[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[CH:4][C:3]=1[C:13]([OH:15])=[O:14]Into a solution of 0.05 mole of 1,4-dihydroxy-2-naphthoic acid in 70 ml. of DMF were dropped, with introduction of nitrogen gas, 10 ml. of a 40% aqueous sodium hydroxide solution and then a solution of 0.05 mole of phenacyl bromide in 10 ml. of DMF, and the resulting mixture was reacted with stirring at 40° C. for 3 to 4 hours. After completion of the reaction, the reaction liquid was poured into ice-hydrochloric acid to deposit crystals, which were then recovered by filtration and recrystallized from acetonitrile to obtain 1-hydroxy-4-benzoylmethoxy-2-naphthoic acid having having a melting point of 190° C. 0.01 Mole of the thus obtained compound and 0.01 mole of N-(δ-2,4-di-tert-amylphenoxy)butylamine were dissolved in 60 ml. of dehydrated dioxane and added with 0.01 mole of dicyclohexyl carbodiimide. The resulting mixture was reacted with stirring at room temperature for 2 hours. After completion of the reaction, the reaction liquid was subjected to filtration, and the filtrate was vaporized under reduced pressure. The residue was charged with n-hexane to deposit crystals, which werethen recoveredby filtration and recrystallized from benzene-n-hexane to obtain a compound having a melting point of 120° to 121° C. (yield 75%). From the measurement of its elementary analysis values and the like, the thus obtained compound was found to be the coupler (1).
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