Potassium Hydroxide → HCID 86235812, compound

HRID 2054158Notes

Reaction equation

HRID 2054158 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[CH:16]=[CH:15][C:12]([CH:13]=[O:14])=[CH:11][CH:10]=2)=[CH:4][CH:3]=1.ClC1C=C(C=CC=1)C(OO)=[O:22].[OH-].[K+]>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([C:9]2[CH:16]=[CH:15][C:12]([CH:13]=[O:14])=[CH:11][CH:10]=2)=[O:22])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 70297m-Chloroperbenzoic acidHCID 4307534HCID 4307534, compound

Product 1

HCID 86235812HCID 86235812, compoundYield 52.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-(4-chlorophenylthio)benzaldehyde (3.63 mmol, 900 mg), 3-chloroperoxybenzoic acid (max 77%, 3.63 mmol, 813 mg) and CH2Cl2 (5.00 mL), was stirred at room temperature for 60 min and poured into a separatory funnel with 5% aqueous KOH solution (10 mL). The phases were separated and the aqueous layer was extracted with CH2Cl2 (3×10 mL) and the combined organic extracts were washed with water (10 mL), brine (50 mL) and dried over MgSO4. Removal of solvents in vacuo gave a light yellow liquid. Purification by flash column chromatography (eluent: 5% EtOAc in Hexane) provided 4-[(4-chlorophenyl)sulfinyl]benzaldehyde (500 mg, 52.2% yield) as a light yellow solid. 1H NMR (CDCl3) δ 10.04 (s, 1H), 7.98 (d, J=8.2 Hz, 2H), 7.82 (d, J=8.2 Hz, 2H), 7.62 (d, J=8.5 Hz, 2H), 7.46 (d, J=8.5 Hz, 2H).

Workup

  1. customThe phases were separated
  2. extractionthe aqueous layer was extracted with CH2Cl2 (3×10 mL)
  3. washthe combined organic extracts were washed with water (10 mL), brine (50 mL)
  4. dry with materialdried over MgSO4
  5. customRemoval of solvents in vacuo
  6. customgave a light yellow liquid
  7. customPurification by flash column chromatography (eluent: 5% EtOAc in Hexane)

Sources & evidence

ORD record
ord-067dc9fde1e241bcb952de09a0af373b
Source dataset
uspto-grants-2008_02
Patent number
US07329656B2

Reaction notes

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