Thiodipropionic Acid → 3,3'-Thiodipropan-1-ol

Participants

Reaction Steps

2.55 g of lithium aluminum hydride are suspended in 100 ml of absolute tetrahydrofuran under argon gasification and treated with a warm solution of 12.0 g of 3,3'-thiodipropionic acid in 100 ml of absolute tetrahydrofuran. After completion of the addition, the resulting heterogenous mixture is heated to reflux for a further 22 hours. After cooling, the mixture is treated with 12.0 ml of saturated potassium carbonate solution, filtered and concentrated. Low-pressure chromatography (0.4 bar) of the resulting colorless oil on silica gel with ethyl acetate and subsequent bulb-tube distillation (150°-170° C./0.15-0.09 mm Hg) gives 2.0 g of 3,3'-thiodi-1-propanol as a colorless, viscous oil; nD23 =1.5088; relative fluorescence: 20 percent for UV excitation, 2 percent for violet excitation, 5 percent for blue excitation.

Provenance & Evidence