1,1'-Dimethyl 2,2'-thiobis(acetate) → Thionyldiacetic acid dimethylester

HRID 1042942Notes

Reaction equation

HRID 1042942 reaction equation
[S:1]([CH2:7][C:8]([O:10][CH3:11])=[O:9])[CH2:2][C:3]([O:5][CH3:6])=[O:4].[O-:12]I(=O)(=O)=O.[Na+]>O.[Cl-].[Na+].O>[S:1]([CH2:2][C:3]([O:5][CH3:6])=[O:4])([CH2:7][C:8]([O:10][CH3:11])=[O:9])=[O:12]

Participants

5

Reactant 2

HCID 852331,1'-Dimethyl 2,2'-thiobis(acetate)HCID 23667635Sodium periodate

Product 1

HCID 10997883Thionyldiacetic acid dimethylesterYield 91.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To the mixture of dimethyl 2,2′-thiodiacetate (4.54 g, 25.5 mmol, 1 eq) in water (50 mL) at 0° C. was added sodium (meta)periodate (5.786 g, 1.05 eq) and the resulting reaction mixture was stirred overnight. The mixture was then diluted with brine and extracted with CHCl3 (5×). All organics were combined and dried with anhydrous sodium sulfate. The solution was decanted, concentrated under reduced pressure, and the clear oily residue was subject to column chromatography (EtOAc-Hex 1:5 to 1:1) giving dimethyl 2,2′-sulfinyldiacetate as a clear oil (4.522 g).

Workup

  1. customthe resulting reaction mixture
  2. extractionextracted with CHCl3 (5×)
  3. dry with materialdried with anhydrous sodium sulfate
  4. customThe solution was decanted
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7f2c0b4afcc249579ce78896f1b23c40
Source dataset
uspto-grants-2013_10
Patent number
US08558002B2

Reaction notes

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