Aluminum(III) Chloride → 1-(2-Sulfanylphenyl)ethan-1-one

HRID 539953Notes

Reaction equation

HRID 539953 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].C([S:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[C:19](=[O:21])[CH3:20])C1C=CC=CC=1>C1C=CC=CC=1>[SH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[C:19](=[O:21])[CH3:20]

Participants

4

Reactant 2

HCID 6451240Aluminum(III) ChlorideHCID 128532331-[2-(Benzylsulfanyl)phenyl]ethan-1-one

Product 1

HCID 110948191-(2-Sulfanylphenyl)ethan-1-oneYield 86.4%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

To a stirred suspension of aluminium chloride (10.50 g, 78.8 mmol) in dry benzene (200 mL) was added a solution of 1-[2-(benzylsulfanyl)phenyl]ethan-1-one (11.93 g, 49.2 mmol) in dry benzene (100 mL) dropwise in an ice bath under argon atmosphere. After the reaction mixture being stirred at room temperature overnight, the reaction was quenched by the cautious addition of ice-water. The separated organic layer was washed with water and extracted with 5% aqueous solution of sodium hydroxide (300 mL). The aqueous layer was acidified to about pH 3 with concentrated hydrochloric acid (12 N) and extracted with dichloromethane (300 mL×3). The combined organic layers were washed with brine, dried over anhydrous sodium sulfate, concentrated in vacuo to afford 6.47 g of the crude product 1-(2-sulfanylphenyl)ethanone.

Workup

  1. customthe reaction was quenched by the cautious addition of ice-water
  2. washThe separated organic layer was washed with water
  3. extractionextracted with 5% aqueous solution of sodium hydroxide (300 mL)
  4. extractionextracted with dichloromethane (300 mL×3)
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-22529d6688fa468788effeec0c2b8099
Source dataset
uspto-grants-2014_10
Patent number
US08871756B2

Reaction notes

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