Methanol → 4-Methyl-1-(prop-2-ynylsulfinyl)benzene

HRID 1816532Notes

Reaction equation

HRID 1816532 reaction equation
I([O-])(=O)(=O)=O.[Na+].C[OH:8].[CH3:9][C:10]1[CH:15]=[CH:14][C:13]([S:16][CH2:17][C:18]#[CH:19])=[CH:12][CH:11]=1>O>[CH3:9][C:10]1[CH:15]=[CH:14][C:13]([S:16]([CH2:17][C:18]#[CH:19])=[O:8])=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 110301514-Methyl-1-prop-2-ynylthiobenzeneHCID 23667635Sodium periodate

Product 1

HCID 117886144-Methyl-1-(prop-2-ynylsulfinyl)benzene

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In 250 mL of water, was subsequently added and dissolved 68.7 g (321 mmol) of sodium periodate. A methanol solution (250 mL) of 49.6 g (306 mmol) of 4-methyl-1-prop-2-ynylthiobenzene [general formula (XI)] was dropped and stirred at room temperature for 2.5 hours. After 2.5 hours, the mixture was filtered, and the solids were washed with 100 mL of ethyl acetate. The filtrate was vacuum concentrated, and 200 mL of water was added. The resulting mixture was extracted with ethyl acetate (150 mL) three times. The obtained organic layers were washed with 150 mL of water, dried with magnesium sulfate and vacuum concentrated to provide 50.6 g (crude yield 93%) of 4-methyl-1-(prop-2-ynylsulfinyl)benzene.

Workup

  1. waitAfter 2.5 hours
  2. filtrationthe mixture was filtered
  3. washthe solids were washed with 100 mL of ethyl acetate
  4. concentrationconcentrated
  5. addition200 mL of water was added
  6. extractionThe resulting mixture was extracted with ethyl acetate (150 mL) three times
  7. washThe obtained organic layers were washed with 150 mL of water
  8. dry with materialdried with magnesium sulfate and vacuum
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-3fc2e77c11d245bab55ebf25d25e7967
Source dataset
uspto-grants-2005_04
Patent number
US06884896B2

Reaction notes

Loading…