Thioanisole → Cyclopentyl[4-(methylsulfanyl)phenyl]methanone

HRID 325180Notes

Reaction equation

HRID 325180 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[CH:5]1([C:10](Cl)=[O:11])[CH2:9][CH2:8][CH2:7][CH2:6]1.[C:13]1([S:19][CH3:20])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C(Cl)(Cl)Cl>[CH:5]1([C:10]([C:16]2[CH:17]=[CH:18][C:13]([S:19][CH3:20])=[CH:14][CH:15]=2)=[O:11])[CH2:9][CH2:8][CH2:7][CH2:6]1

Participants

5

Reactant 3

HCID 7520ThioanisoleHCID 78284Cyclopentanecarbonyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 22002634Cyclopentyl[4-(methylsulfanyl)phenyl]methanoneYield 93.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a suspension of anhydrous aluminum chloride (9.3 g, 69.6 mmol) in 58 mL CHCl3 at 0° C. was added dropwise cyclopentanecarbonyl chloride (10.0 g, 75.4 mmol), followed by thioanisole (7.21 g, 58.0 mmol). The ice bath was removed and the mixture was stirred at room temperature for 2 h. Water (200 ml) was added with cooling, the layers were separated and the aqueous layer was extracted with CHCl3 (3×50 mL). The combined aqueous layers were dried over MgSO4, filtered and concentrated. The residue was chromatographed on silica gel (4% EtOAc/hexane) to give 11.9 g of the title ketone (93%).

Workup

  1. customThe ice bath was removed
  2. additionWater (200 ml) was added
  3. temperaturewith cooling
  4. customthe layers were separated
  5. extractionthe aqueous layer was extracted with CHCl3 (3×50 mL)
  6. dry with materialThe combined aqueous layers were dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was chromatographed on silica gel (4% EtOAc/hexane)

Sources & evidence

ORD record
ord-70bee4eab9e342adbdda1faceab7a5a2
Source dataset
uspto-grants-2001_04
Patent number
US06222048B1

Reaction notes

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