[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[OH-].[Na+:16].Cl[CH2:18][S:19]([O-:22])(=[O:21])=[O:20].[Na+]>O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH2:18][S:19]([O-:22])(=[O:21])=[O:20])=[CH:10][CH:9]=2)=[CH:6][CH:7]=1.[Na+:16]In a 1-liter round-bottomed flask is placed 4-(4-chlorophenyl)phenol (25.5 g.), 4.0 N aqueous sodium hydroxide (39.0 ml.) and water (75 ml.). The mixture is heated to 90°-100° C., and sodium chloromethyl sulphonate (46.5 g.) is added. The mixture is heated rapidly to 160°-170° C. (bath temperature) while a current of air is passed through the flask. When most of the water has been removed the temperature of the bath is raised to, and kept at, 220°-225° C., for 90 minutes; the mixture is then cooled. The solid cakes obtained from two identical experiments are ground with water (200 ml.) in a mortar. The resulting suspension is heated to 80° C. and allowed to cool slowly, then filtered. The product is washed with water and dried to give sodium 4-(4-chlorophenyl)phenoxymethylsulphonate (58.4 g.) as a cream coloured powder pure enough for use. It may be further purified by crystallisation from aqueous dimethylsulphoxide and obtained as a microcrystalline powder not melting at 300° C.
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