Ethylene Glycol → HCID 59676556, compound

HRID 1391998

Reaction equation

HRID 1391998 reaction equation
[CH2:1]([OH:4])[CH2:2][OH:3].[SH:5][C:6]([CH3:11])([CH3:10])[C:7]([OH:9])=O.O.C1(C)C=[CH:17][C:16]([S:19](O)(=O)=O)=[CH:15]C=1.[C:24](=[O:27])([O-])O.[Na+]>C1(C)C=CC=CC=1>[SH:19][C:16]([CH3:17])([CH3:15])[C:24]([O:3][CH2:2][CH2:1][O:4][C:7](=[O:9])[C:6]([SH:5])([CH3:11])[CH3:10])=[O:27]

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 784212-Mercapto-2-methylpropanoic acidHCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrate3×

Product 1

HCID 59676556HCID 59676556, compound

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, 15.86 g (132 mmol) of 2-mercaptoisobutanoic acid (manufactured by Yodo Chemical Co., Ltd.), 0.92 g (4.8 mmol) of p-toluenesulfonic acid monohydrate, and 60 g of toluene, 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 after 5 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 2 hours, 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. Then, the toluene was distilled off and the residue was subjected to column chromatography with silica gel to purify EGMIB. 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 EGMIB obtained by the purification was a white crystal and the yield was 6.08 g (38%). The EGMIB 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. additionwas added
  4. waitthe reaction mixture was left
  5. temperatureto cool
  6. washFurther, the reaction mixture was washed with deionized water three times
  7. dry with materialdried over anhydrous magnesium sulfate
  8. distillationThen, the toluene was distilled off
  9. customto purify EGMIB
  10. customThe EGMIB obtained by the purification

Sources & evidence

ORD record
ord-1f70a031a2b547c9b6426942e3f45f5d
Source dataset
uspto-grants-2008_03
Patent number
US07341828B2

Linked notes

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