Sodium Hydroxide → 2-(Cyclohexylsulfonyl)benzaldehyde

HRID 1919848Notes

Reaction equation

HRID 1919848 reaction equation
[CH:1]1([S:7][C:8]2[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=2[CH:10]=[O:11])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C1C=C(Cl)C=C(C(OO)=[O:24])C=1.[OH-:27].[Na+]>C(Cl)Cl.C1C=C(Cl)C=C(C(OO)=O)C=1>[CH:1]1([S:7]([C:8]2[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=2[CH:10]=[O:11])(=[O:24])=[O:27])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 70297m-Chloroperbenzoic acidHCID 63801869HCID 63801869, compound

Product 1

HCID 866330192-(Cyclohexylsulfonyl)benzaldehydeYield 91%

Reagents, catalysts & solvents 2

HCID 70297m-Chloroperbenzoic acidCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 2-(cyclohexylthio)benzaldehyde (3.22 g, 14.6 mmol) in DCM (100 mL) at 0° C. was added mCPBA (70-77% wt in water, 7.17 g, 30.7 mmol) portionwise over 30 minutes, then stirred for 1 hour at 0° C. Additional mCPBA (150 mg, 0.6 mmol) was added and stirred for a further 30 minutes, before aqueous 1N NaOH was added to the reaction mixture and stirred vigorously for 5 minutes. The product was extracted with DCM, and the combined organic phase washed successively with 1N NaOH, then saturated brine, dried over anhydrous magnesium sulfate, filtered and evaporated in vacuo to afford 2-(cyclohexylsulfonyl)benzaldehyde (3.34 g, 13.2 mmol, 91%) as a white solid.

Workup

  1. additionwas added to the reaction mixture
  2. stirringstirred vigorously for 5 minutes
  3. extractionThe product was extracted with DCM
  4. washthe combined organic phase washed successively with 1N NaOH
  5. dry with materialsaturated brine, dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-a6b7a14106104326aa44dd81f1314c7e
Source dataset
uspto-grants-2012_05
Patent number
US08168673B2

Reaction notes

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