m-Chloroperbenzoic acid → 2-[(4-Chlorophenyl)sulfonyl]benzaldehyde

HRID 2387567Notes

Reaction equation

HRID 2387567 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5](SC2C=CC=CC=2C=O)=[CH:4][CH:3]=1.Cl[C:18]1[CH:19]=[C:20]([CH:25]=[CH:26][CH:27]=1)[C:21]([O:23]O)=O.[S:28](S([O-])=O)([O-:31])(=O)=[O:29].[Na+].[Na+]>ClCCl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:28]([C:19]2[CH:18]=[CH:27][CH:26]=[CH:25][C:20]=2[CH:21]=[O:23])(=[O:31])=[O:29])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 656671Sodium PyrosulfiteHCID 27786242-(4-Chlorophenylthio)Benzaldehyde

Product 1

HCID 866589052-[(4-Chlorophenyl)sulfonyl]benzaldehydeYield 46%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(4-chlorophenylthio)benzaldehyde (2.00 g, 8.00 mmol) in dichloromethane (20 mL) at 0° C. was added meta chloroperoxybenzoic acid (77% max, 5.40 g, 24.17 mmol) in, portions over 15 minutes, then warmed to room temperature and stirred for 2 hours. Aqueous sodium metabisulfite solution was added carefully until effervescence ceased. This solution was extracted with dichloromethane and the combined organic extracts were washed with NaOH (1N) then saturated brine, dried over MgSO4 and concentrated in vacuo giving a white solid (1.05 g, 3.74 mmol, 46%). δH (300 MHz, d6-DMSO) 10.69 (1H, s, CHO), 8.25-8.18 (1H, m, Ar), 8.07-8.00 (2H, m, Ar), 8.00-7.90 (3H, m, Ar) and 7.81-7.64 (3H, m, Ar).

Workup

  1. extractionThis solution was extracted with dichloromethane
  2. washthe combined organic extracts were washed with NaOH (1N)
  3. dry with materialsaturated brine, dried over MgSO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-06f4df00109448608fae54363a4d7e2f
Source dataset
uspto-grants-2012_09
Patent number
US08268878B2

Reaction notes

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