m-Chloroperbenzoic acid → 2-(4-Methanesulfinyl-phenyl)-[1,3]dioxane

HRID 1828706Notes

Reaction equation

HRID 1828706 reaction equation
[CH3:1][S:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[O:14][CH2:13][CH2:12][CH2:11][O:10]2)=[CH:5][CH:4]=1.C1C=C(Cl)C=C(C(OO)=[O:23])C=1>C(Cl)Cl>[CH3:1][S:2]([C:3]1[CH:4]=[CH:5][C:6]([CH:9]2[O:10][CH2:11][CH2:12][CH2:13][O:14]2)=[CH:7][CH:8]=1)=[O:23]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 220577452-(4-Methylsulfanyl-phenyl)-[1,3]dioxane

Product 1

HCID 220577372-(4-Methanesulfinyl-phenyl)-[1,3]dioxane

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2-(4-methylsulfanyl-phenyl)-[1,3]dioxane (2 g, 9.5 mmol) in DCM (50 mL) at 0° C. is added m-CPBA (2.46 g, 10.5 mmol). The mixture is stirred at 0° C. for 1 h after which Ca(OH)2 (770 mg, 10.5 mmol.) is added. The reaction is stirred an additional 30 min, then the reaction mixture is diluted with DCM and filtered through celite. The filtrate is collected and concentrated to give 2-(4-methanesulfinyl-phenyl)-[1,3]dioxane as a white solid.

Workup

  1. additionis added
  2. filtrationfiltered through celite
  3. customThe filtrate is collected
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-5d99073426e2484ebef74881650a427f
Source dataset
uspto-grants-2006_06
Patent number
US07060697B2

Reaction notes

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