Sodium Chloride → 4-(Benzenesulfinyl)-3-methylbutan-1-ol

HRID 746293Notes

Reaction equation

HRID 746293 reaction equation
[C:1]1([S:7][CH2:8][CH:9]([CH3:13])[CH2:10][CH2:11][OH:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.I([O-])(=O)(=O)=[O:15].[Na+].[Cl-].[Na+]>CO.O>[C:1]1([S:7]([CH2:8][CH:9]([CH3:13])[CH2:10][CH2:11][OH:12])=[O:15])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 5234Sodium ChlorideHCID 133582273-Methyl-4-(phenylsulfanyl)butan-1-olHCID 23667635Sodium periodate

Product 1

HCID 140810454-(Benzenesulfinyl)-3-methylbutan-1-ol

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

1.96 g of 4-phenylthio-3-methyl-1-butanol were dissolved in 100 ml of methanol, a solution of 2.57 g of sodium metaperiodate in 50 ml of water added, and the mixture stirred at room temperature overnight. Then, an aqueous solution of sodium chloride was added, the resulting mixture extracted with diethyl ether, the ether layer washed with water and a saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate, and the ether distilled off. There was obtained a slightly yellow liquid. This was purified by silica gel column chromatography (developing solvent: methylene chloride-ethyl acetate) to give 1.60 g of a colorless to slightly yellow liquid. The characteristic signals of this substance on its 1H-NMR spectrum were as follows:

Workup

  1. extractionthe resulting mixture extracted with diethyl ether
  2. washthe ether layer washed with water
  3. dry with materiala saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate
  4. distillationthe ether distilled off
  5. customThere was obtained a slightly yellow liquid
  6. customThis was purified by silica gel column chromatography (developing solvent: methylene chloride-ethyl acetate)
  7. customto give 1.60 g of a colorless to slightly yellow liquid

Sources & evidence

ORD record
ord-de4c6f15ce5d444683a95b8b90cabdba
Source dataset
uspto-grants-1986_07
Patent number
US04603208

Reaction notes

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