Ethylene Glycol → Ethylene Glycol bis(3-mercaptobutyrate)

HRID 1391995Notes

Reaction equation

HRID 1391995 reaction equation
[CH2:1]([OH:4])[CH2:2][OH:3].[SH:5][CH:6]([CH3:11])[CH2:7][C:8]([OH:10])=O.O.C1(C)C=[CH:17][C:16]([S:19](O)(=O)=O)=[CH:15][CH:14]=1.[Na].C(=O)([O-])[OH:26]>C1(C)C=CC=CC=1>[SH:19][CH:16]([CH3:17])[CH2:15][C:14]([O:3][CH2:2][CH2:1][O:4][C:8](=[O:10])[CH2:7][CH:6]([SH:5])[CH3:11])=[O:26]

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 521998p-Toluenesulfonic acid monohydrate3×HCID 99640843-Mercaptobutyric acidHCID 50987224Sodium hydrogen-carbonate

Product 1

HCID 15752074Ethylene Glycol bis(3-mercaptobutyrate)

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
140 °C

Procedure

In a 200-ml eggplant-shaped flask were charged 3.72 g (60 mmol) of ethylene glycol (manufactured by Wako Pure Chemical Industry Co., Ltd.), 15.86 g (132 mmol) of 3-mercaptobutanoic acid (manufactured by Yodo Chemical Co., Ltd.), 0.92 g (4.8 mmol) of p-toluenesulfonic acid monohydrate (manufactured by Junsei Chemicals Co., Ltd.), and 60 g of toluene (manufactured by Junsei Chemicals Co., Ltd.), and a Dean-Stark apparatus and a condenser tube were equipped thereto. While the contents being stirred, they were heated at an oil bath temperature of 140° C. After 2 hours from the start of the reaction, 0.92 g (4.8 mmol) of p-toluenesulfonic acid monohydrate was added and further after 4 hours from the start of the reaction, 0.46 g (2.4 mmol) of p-toluenesulfonic acid monohydrate was added. Further, after the reaction was performed for another 1 hour, the reaction mixture was left to cool and neutralized with 200 ml of an aqueous 10% sodium-hydrogen carbonate solution. Further, the reaction mixture was washed with deionized water three times, and then dehydrated and dried over anhydrous magnesium sulfate (manufactured by Junsei Chemicals Co., Ltd.). Then, the toluene was distilled off and the residue was subjected to column chromatography with silica gel to purify EGMB. The silica gel used was Wako Gel C-200 (manufactured by Wako Pure Chemical Industry Co., Ltd.), and n-hexane/ethyl acetate=6/1 (by volume ratio) was used as an elution solvent. The EGMB obtained by the purification was a colorless transparent liquid and the yield was 7.57 g (45%). The EGMB had a compositional formula of C10H18O4S2 and a molecular weight of 266.38.

Workup

  1. customa Dean-Stark apparatus and a condenser tube were equipped
  2. additionwas added
  3. waitthe reaction mixture was left
  4. temperatureto cool
  5. washFurther, the reaction mixture was washed with deionized water three times
  6. dry with materialdried over anhydrous magnesium sulfate (manufactured by Junsei Chemicals Co., Ltd.)
  7. distillationThen, the toluene was distilled off
  8. customto purify EGMB
  9. customThe EGMB obtained by the purification

Sources & evidence

ORD record
ord-b7e50f6294ff4ccfb739ce58c7ca4f61
Source dataset
uspto-grants-2008_03
Patent number
US07341828B2

Reaction notes

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