I[C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[SH:11][C:12]1[CH:21]=[CH:20][C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:13]=1.C(=O)([O-])[O-].[K+].[K+].N1C=CC=CC=1>O>[CH:13]1[C:14]2[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:20]=[CH:21][C:12]=1[S:11][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]A well stirred mixture of 37.2 g. (0.15 mole) of o-iodobenzoic acid, 34.0 g. (0.15 mole) of 2-mercaptonaphthalene, 20.6 g. (0.15 mole) of potassium carbonate and 300 ml. of pyridine is heated at 50° C. for 1 hour, then 5 g. of cuprous chloride is added and the stirred mixture is heated at reflux for 18 hours. The mixture is poured into 1.2 liters of water and filtered. The filtrate is acidified and the resulting mixture is extracted into methylene chloride. The extracts are dried, concentrated, and the solid residue is recrystallized to give 2-(2-naphthylthio)benzoic acid.
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