Trimethylolpropane → Trimethylolpropane tris(3-mercaptobutyrate)

HRID 1391997Notes

Reaction equation

HRID 1391997 reaction equation
[CH2:1]([C:3]([CH2:8][OH:9])([CH2:6][OH:7])[CH2:4][CH3:5])[OH:2].[SH:10][CH:11]([CH3:16])[CH2:12][C:13]([OH:15])=[O:14].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)([O-])O.[Na+]>C1(C)C=CC=CC=1>[SH:10][CH:11]([CH3:16])[CH2:12][C:13]([OH:15])=[O:14].[SH:10][CH:11]([CH3:16])[CH2:12][C:13]([OH:15])=[O:14].[SH:10][CH:11]([CH3:16])[CH2:12][C:13]([OH:15])=[O:14].[CH2:1]([C:3]([CH2:8][OH:9])([CH2:6][OH:7])[CH2:4][CH3:5])[OH:2]

Participants

6

Reactant 4

HCID 6510TrimethylolpropaneHCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 99640843-Mercaptobutyric acid

Product 1

HCID 86599594Trimethylolpropane tris(3-mercaptobutyrate)

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 3-mercaptobutanoic acid, 0.23 g (1.2 mmol) of p-toluenesulfonic acid monohydrate, 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 TPMB. 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 TPMB obtained by the purification was a colorless transparent liquid and the yield was 5.63 g (64%). The TPMB had a compositional formula of C18H32O6S3 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 TPMB
  9. customThe TPMB obtained by the purification

Sources & evidence

ORD record
ord-c87d892e05cb4bebb87b5e2c2ca2df3b
Source dataset
uspto-grants-2008_03
Patent number
US07341828B2

Reaction notes

Loading…