[SH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([SH:14])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[OH-].[Na+].O.Cl[CH2:19][CH2:20][OH:21].[CH2:22]([OH:24])[CH3:23]>>[OH:21][CH2:20][CH2:19][S:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([S:14][CH2:23][CH2:22][OH:24])=[CH:10][CH:9]=2)=[CH:6][CH:7]=1A mixture of 4,4'-dimercaptobiphenyl (41.7 grams, 0.19 mole), 50% NaOH [31.2 grams (15.6 grams, 0.39 mole NaOH)], water (100 mL) and 2 β ethanol (60 mL) was heated under nitrogen under stirring while 2-chloroethanol (31.5 grams, 0.39 mole) was added dropwise at reflux. When addition was completed, additional 2 β ethanol (60 mL) was added to facilitate stirring. After being heated an additional 2.0 hours at reflux, the reaction mixture was allowed to cool and the product was collected by vacuum filtration, washed with water and dried in air.
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