Methanol → 1,3-Bis(2-hydroxyethylthio)propane
Reaction equation
[Na+].[SH-:2].[SH:3][CH2:4][CH2:5][OH:6].[CH3:7][O-:8].[Na+].Cl[CH2:11][CH2:12][CH2:13]Cl.[CH3:15]O>>[OH:6][CH2:5][CH2:4][S:3][CH2:11][CH2:12][CH2:13][S:2][CH2:15][CH2:7][OH:8][Na+].[SH-:2].[SH:3][CH2:4][CH2:5][OH:6].[CH3:7][O-:8].[Na+].Cl[CH2:11][CH2:12][CH2:13]Cl.[CH3:15]O>>[OH:6][CH2:5][CH2:4][S:3][CH2:11][CH2:12][CH2:13][S:2][CH2:15][CH2:7][OH:8]The sodium mercaptide of 2-mercaptoethanol was made by reacting 1 mole each of sodium methoxide and 2-mercaptoethanol in dry methanol under a nitrogen atmosphere. To this solution, 0.5 mole of 1,3-dichloropropane was added and the mixture was refluxed for 1 hour and filtered. The methanol filtrate was evaporated on a flash evaporator and traces of 2-mercaptoethanol were distilled off at high vacuum at room temperature. The yellow, oily residue was extracted with acetone, the solution filtered, and the acetone evaporated to give a 95 percent yield of the crude product.
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