Potassium Iodide → 3-Hydroxypropyl 4-methylbenzenesulfonate

HRID 2059525Notes

Reaction equation

HRID 2059525 reaction equation
[CH2:1]([OH:5])[CH2:2][CH2:3][OH:4].[I-].[K+].[C:8]1([CH3:18])[CH:13]=[CH:12][C:11]([S:14](Cl)(=[O:16])=[O:15])=[CH:10][CH:9]=1>C(Cl)Cl.[Ag]=O>[C:8]1([CH3:18])[CH:13]=[CH:12][C:11]([S:14]([O:4][CH2:3][CH2:2][CH2:1][OH:5])(=[O:16])=[O:15])=[CH:10][CH:9]=1

Participants

6

Reactant 3

HCID 4875Potassium IodideHCID 73974-Toluenesulfonyl chlorideHCID 104421,3-Propanediol

Product 1

HCID 119613563-Hydroxypropyl 4-methylbenzenesulfonateYield 53.5%

Reagents, catalysts & solvents 2

HCID 92152Silver(II) oxideCatalystHCID 6344DichloromethaneSolvent

Procedure

1.45 mL (corresponding to 20.0 mmol) of 1,3-propanediol was dissolved in 200 mL of methylene chloride. To this solution under an ice bath, 6.96 g (corresponding to 30.0 mmol) of silver oxide, 666 mg (corresponding to 4.0 mmol) of potassium iodide and 4.21 g (corresponding to 22.0 mmol) of p-toluenesulfonyl chloride were added. The resulting mixture was stirred at room temperature for 3 hours. Insoluble matters were filtered out of the reaction mixture, and were washed with ethyl acetate. The washings were combined with the filtrate, and the mixture was concentrated. The resulting crude product was purified with flash silica gel column chromatography (elution solvent: hexane/ethyl acetate=3/2 to 1/1) to obtain 2.47 g (corresponding to 10.7 mmol) of 1,3-propanediol mono-p-toluenesulfonate (FIG. 1, Step 6).

Workup

  1. filtrationInsoluble matters were filtered out of the reaction mixture
  2. washwere washed with ethyl acetate
  3. concentrationthe mixture was concentrated
  4. customThe resulting crude product was purified with flash silica gel column chromatography (elution solvent: hexane/ethyl acetate=3/2 to 1/1)

Sources & evidence

ORD record
ord-c4118500adee4f2098228f0201e4ab83
Source dataset
uspto-grants-2012_10
Patent number
US08277777B2

Reaction notes

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