Water → HCID 18546538, compound

HRID 1267527Notes

Reaction equation

HRID 1267527 reaction equation
S(O[CH2:12][CH2:13][CH2:14][S:15][CH3:16])(C1C=CC(C)=CC=1)(=O)=O.[SH:17][CH2:18][CH2:19][CH2:20][OH:21].CC(C)([O-])C.[K+].O>C1COCC1>[CH2:20]([OH:21])[CH2:19][CH2:18][S:17][CH2:12][CH2:13][CH2:14][S:15][CH3:16]

Participants

6

Reactant 4

HCID 962WaterHCID 882113-MercaptopropanolHCID 153109983-(Methylthio)propyl 4-methylbenzenesulfonateHCID 23665647Potassium tert-butoxide

Product 1

HCID 18546538HCID 18546538, compoundYield 88.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 3-methylthio-1-propanol tosylate (14.14 g, 54.3 mmol), and 3-mercapto-1-propanol (5.0 g, 54.3 mmol) in dry THF (300 mL) was added potassium tert-butoxide (8.51 g, 80.0 mmol) in one portion under a blanket of nitrogen, and the resulting mixture was stirred at room temperature for 24 hours. Water (10 mL) was added drop-wise to the reaction mixture to quench excess potassium tert-butoxide, and solvent was evaporated under reduced pressure. The resulting solid was washed with ether (3×100 mL), and filtered. The ether layer was washed with water (3×100 mL) and dried (Na2SO4). Solvent evaporation produced 8.7 g of a light yellow oil. This product was used for acryloylation without further purification.

Workup

  1. customto quench excess potassium tert-butoxide, and solvent
  2. customwas evaporated under reduced pressure
  3. washThe resulting solid was washed with ether (3×100 mL)
  4. filtrationfiltered
  5. washThe ether layer was washed with water (3×100 mL)
  6. dry with materialdried (Na2SO4)
  7. customSolvent evaporation

Sources & evidence

ORD record
ord-f42c37e02537499cbfb8ffea9d200b47
Source dataset
uspto-grants-2003_04
Patent number
US06552103B1

Reaction notes

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