Trimethylolpropane → Trimethylolpropane tris(2-mercaptoisobutyrate)

HRID 1392000Notes

Reaction equation

HRID 1392000 reaction equation
[CH2:1]([C:3]([CH2:8][OH:9])([CH2:6][OH:7])[CH2:4][CH3:5])[OH:2].[SH:10][C:11]([CH3:16])([CH3:15])[C:12]([OH:14])=[O:13].CC1C=CC(S(O)(=O)=O)=CC=1.O.C(=O)([O-])O.[Na+]>C1(C)C=CC=CC=1>[SH:10][C:11]([CH3:16])([CH3:15])[C:12]([OH:14])=[O:13].[SH:10][C:11]([CH3:16])([CH3:15])[C:12]([OH:14])=[O:13].[SH:10][C:11]([CH3:16])([CH3:15])[C:12]([OH:14])=[O:13].[CH2:1]([C:3]([CH2:8][OH:9])([CH2:6][OH:7])[CH2:4][CH3:5])[OH:2]

Participants

6

Reactant 4

HCID 6510TrimethylolpropaneHCID 784212-Mercapto-2-methylpropanoic acidHCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 86599597Trimethylolpropane tris(2-mercaptoisobutyrate)

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
145 °C

Procedure

In a 100-ml eggplant-shaped flask were charged 2.68 g (20 mmol) of trimethylolpropane (manufactured by Tokyo Kasei Kogyo Co., Ltd.), 7.57 g (63 mmol) of 2-mercaptoisobutanoic acid, 0.23 g (1.2 mmol) of p-toluenesulfonic acidmonohydrate, and 20 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 145° C. After 3 hours from the start of the reaction, the reaction mixture was left to cool and neutralized with 50 ml of an aqueous 5% sodium hydrogen carbonate solution. Further, the reaction mixture was washed with deionized water two 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 TPMIB. The silica gel used was Wako Gel C-200, and n-hexane/ethyl acetate=5/1 (by volume ratio) was used as an elution solvent. The TPMIB obtained by the purification was a white crystal and the yield was 4.50 g (51%). The TPMIB had a compositional formula of Cl18H32O6S3 and a molecular weight of 440.64.

Workup

  1. customa Dean-Stark apparatus and a condenser tube were equipped
  2. customAfter 3 hours from the start of the reaction
  3. waitthe reaction mixture was left
  4. temperatureto cool
  5. washFurther, the reaction mixture was washed with deionized water two times
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationThen, the toluene was distilled off
  8. customto purify TPMIB
  9. customThe TPMIB obtained by the purification

Sources & evidence

ORD record
ord-d615ad357d134a70b7879b8ccaba5733
Source dataset
uspto-grants-2008_03
Patent number
US07341828B2

Reaction notes

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