Ethyl Acetate → 2-(Methanesulfinyl)benzaldehyde

HRID 1040401Notes

Reaction equation

HRID 1040401 reaction equation
[CH3:1][S:2][C:3]1[CH:10]=[CH:9][CH:8]=[CH:7][C:4]=1[CH:5]=[O:6].C(OCC)(=[O:13])C>ClCCl>[CH3:1][S:2]([C:3]1[CH:10]=[CH:9][CH:8]=[CH:7][C:4]=1[CH:5]=[O:6])=[O:13]

Participants

4

Reactant 2

HCID 8857Ethyl AcetateHCID 2864432-(Methylthio)benzaldehyde

Product 1

HCID 123473352-(Methanesulfinyl)benzaldehydeYield 89%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(methylthio)benzaldehyde (500 mg, 3.28 mmol) in 6.6 mL of dichloromethane was added m-chlorobenzoic peracid (0.85 g, 4.9 mmol) at 0° C. After being stirred at room temperature for 1 h, the reaction mixture was diluted with ethyl acetate. The solution was washed with saturated NaHCO3 aqueous solution, brine, and dried over MgSO4. After filtration, the filtrate was concentrated in vacuo, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate=50/50 to 15/85) to obtain the title compound as a white crystal (493 mg, 89%).

Workup

  1. washThe solution was washed with saturated NaHCO3 aqueous solution, brine
  2. dry with materialdried over MgSO4
  3. filtrationAfter filtration
  4. concentrationthe filtrate was concentrated in vacuo
  5. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate=50/50 to 15/85)

Sources & evidence

ORD record
ord-95d93b6bcaac4cc793b14a88fd6fbcbc
Source dataset
uspto-grants-2013_10
Patent number
US08552220B2

Reaction notes

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