2-Chloroethanol → HCID 2192654, compound

Reaction equation

[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]=1

Participants

Reactant 5

HCID 342-Chloroethanol

HCID 702Ethanol2×

HCID 962Water

HCID 14798Sodium Hydroxide

HCID 813994,4'-Thiobiphenyl

Product 1

HCID 2192654HCID 2192654, compound

Procedure

A 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.