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

HRID 1489047Notes

Reaction equation

HRID 1489047 reaction equation
[C:1]1([CH2:7][C:8](Cl)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:11]1([S:17][CH3:18])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.O>C(Cl)(Cl)Cl>[CH3:18][S:17][C:11]1[CH:16]=[CH:15][C:14]([C:8](=[O:9])[CH2:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 962WaterHCID 7520ThioanisoleHCID 7679Phenylacetyl 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 AICl3 (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 water 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-65f748ea12de40b1a5df2adc4a8c5ea9
Source dataset
uspto-grants-1997_10
Patent number
US05677318

Reaction notes

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