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

HRID 2412521Notes

Reaction equation

HRID 2412521 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[S:7]([CH2:13][CH2:14][C:15](O)=[O:16])[CH2:8][CH2:9][C:10](O)=[O:11].C(=O)([O-])[O-].[K+].[K+]>O1CCCC1>[S:7]([CH2:13][CH2:14][CH2:15][OH:16])[CH2:8][CH2:9][CH2:10][OH:11]

Participants

5

Reactant 3

HCID 8096Thiodipropionic AcidHCID 11430Potassium CarbonateHCID 21226445Aluminium lithium hydride

Product 1

HCID 663583,3'-Thiodipropan-1-olYield 19.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

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.

Workup

  1. additionAfter completion of the addition
  2. temperaturethe resulting heterogenous mixture is heated
  3. temperatureto reflux for a further 22 hours
  4. temperatureAfter cooling
  5. filtrationfiltered
  6. concentrationconcentrated
  7. distillationLow-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)

Sources & evidence

ORD record
ord-59b739a1037f4d9da54252c0e5fdaf08
Source dataset
uspto-grants-1985_01
Patent number
US04493533

Reaction notes

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