Pentaerythritol → Pentaerythritol tris(3-mercaptobutyrate)

HRID 555207

Reaction equation

HRID 555207 reaction equation
[OH:1][CH2:2][C:3]([CH2:8][OH:9])([CH2:6][OH:7])[CH2:4][OH:5].[SH:10][CH:11]([CH3:16])[CH2:12][C:13]([OH:15])=O.[OH2:17].C1(C)[CH:23]=[CH:22][C:21]([S:24](O)(=O)=O)=[CH:20]C=1.[C:29](=[O:32])([O-])O.[Na+]>C1(C)C=CC=CC=1>[SH:24][CH:21]([CH3:20])[CH2:22][C:23]([O:1][CH2:2][C:3]([CH2:8][OH:9])([CH2:6][O:7][C:29](=[O:32])[CH2:12][CH:11]([SH:10])[CH3:16])[CH2:4][O:5][C:13](=[O:15])[CH2:12][CH:11]([SH:10])[CH3:16])=[O:17]

Participants

6

Reactant 4

HCID 8285PentaerythritolHCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrate2×HCID 99640843-Mercaptobutyric acid2×

Product 1

HCID 54578067Pentaerythritol tris(3-mercaptobutyrate)Yield 47%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
130 °C

Procedure

A 200 ml three-necked flask was charged with 15.0 g (110.2 mmol) of pentaerythritol (manufactured by TOKYO CHEMICAL INDUSTRY CO., LTD.), 26.5 g (220.3 mmol) of 3-mercaptobutanoic acid (manufactured by YODO KAGAKU CO., LTD.), 1.8 g (9.3 mmol) of p-toluenesulfonic acid monohydrate (manufactured by JUNSEI CHEMICAL CO., LTD.) and 35 g of toluene (manufactured by JUNSEI CHEMICAL CO., LTD.). A Dean-Stark apparatus and a condenser tube were attached. The materials were heated in an oil bath at 130° C. with stirring. After 4 hours after the reaction was initiated, 13.3 g (110.1 mmol) of 3-mercaptobutanoic acid was added. Further, 0.85 g (4.5 mmol) of p-toluenesulfonic acid monohydrate was added after 6 hours from the initiation of the reaction. The reaction was carried out for another 4 hours. The reaction liquid was allowed to cool, was neutralized with 200 ml of a saturated aqueous sodium hydrogen carbonate solution, and was washed twice with 200 ml of pure water. The reaction liquid was then dehydrated and dried over anhydrous magnesium sulfate (manufactured by JUNSEI CHEMICAL CO., LTD.) and was distilled to remove the toluene, thereby giving a mixture containing the target compound. PE3MB obtained was a colorless transparent liquid and weighed 22.5 g, providing 47% yield. The composition formula of PE3MB was C17H30O7S3 and the molecular weight was 442.61.

Workup

  1. waitThe reaction was carried out for another 4 hours
  2. customThe reaction liquid
  3. temperatureto cool
  4. washwas washed twice with 200 ml of pure water
  5. customThe reaction liquid
  6. dry with materialdried over anhydrous magnesium sulfate (manufactured by JUNSEI CHEMICAL CO., LTD.)
  7. distillationwas distilled
  8. customto remove the toluene
  9. customgiving a mixture
  10. additioncontaining the target compound
  11. customPE3MB obtained
  12. customproviding 47% yield

Sources & evidence

ORD record
ord-7bb5aba4008d4c34823c0305217766b5
Source dataset
uspto-grants-2011_11
Patent number
US08053167B2

Linked notes

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