Thioanisole → 1-(4-(methylthio)phenyl)-2-phenylethanone

HRID 741687Notes

Reaction equation

HRID 741687 reaction equation
[C:1]1([CH2:7][C:8](Cl)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Al+3].[Cl-].[Cl-].[Cl-].[C:15]1([S:21][CH3:22])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C(Cl)(Cl)Cl>[CH3:22][S:21][C:15]1[CH:20]=[CH:19][C:18]([C:8](=[O:9])[CH2:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 7520ThioanisoleHCID 7679Phenylacetyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 27600881-(4-(methylthio)phenyl)-2-phenylethanoneYield 64.4%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a cold (0° C.) solution of phenylacetyl chloride (92.8 g, 0.6 mol) in CHCl3 (1.2 L) was added AlCl3 (80 g, 0.6 mol) in portions. Thioanisole (62.1 g, 0.5 mol) was then added dropwise. The resulting mixture was stirred at r.t. for 1.5 h. The mixture was poured into 4 L of ice and extracted with CHCl3. The combined organic extracts were dried over MgSO4, filtered and concentrated. The residue was slurried in 300 mL of 20 % EtOAc/hexane, filtered and washed with hexane to give 78 g of the title compound.

Workup

  1. extractionextracted with CHCl3
  2. dry with materialThe combined organic extracts were dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. filtrationfiltered
  6. washwashed with hexane

Sources & evidence

ORD record
ord-a6a097ed0fc64b7dbbd0fe62419cbf75
Source dataset
uspto-grants-1996_09
Patent number
US05552422

Reaction notes

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