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

HRID 1358162Notes

Reaction equation

HRID 1358162 reaction equation
[C:1]1([S:7][CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Al+3].[Cl-].[Cl-].[Cl-].[C:13]1([CH2:19][C:20](Cl)=[O:21])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C(Cl)Cl>[CH3:8][S:7][C:1]1[CH:6]=[CH:5][C:4]([C:20](=[O:21])[CH2:19][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:3][CH:2]=1

Participants

5

Reactant 3

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

Product 1

HCID 27600881-(4-(methylthio)phenyl)-2-phenylethanoneYield 85.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

Thioanisole (6.22 g, 50 mmol) I) diliuted with CH2Cl2 (5 ml) is added to a suspension of AlCl3. (6.8 g, 51 mmol) in 45 ml of CH2Cl2. Phenylacetyl chloride (7.73 g, 50.0 mmol) in CH2Cl2 (15 ml) is added dropwise at 0° C. over 5 min. Then, the reaction solution is gradually warmed up to room temperature and stirred overnight. The reaction solution is poured onto ice. The resulting white precipitate is extracted with CH2Cl2, and the organic layer is washed with water and NaHCO3 aq. solution, followed by drying over anhydrous MgSO4. After evaporating the solvent, the residue is purified by recrystallization from hexane-CH2Cl2. 10.4 g of a white solid are obtained (86%). 1H NMR (CDCl3), δ[ppm]: d 2.50 (s, 3H), 4.23 (s, 2H), 7.22-7.27 (m, 5H), 7.32 (t, 2H), 7.91 (d, 2H)

Workup

  1. additionThe reaction solution is poured onto ice
  2. extractionThe resulting white precipitate is extracted with CH2Cl2
  3. washthe organic layer is washed with water and NaHCO3 aq. solution
  4. dry with materialby drying over anhydrous MgSO4
  5. customAfter evaporating the solvent
  6. customthe residue is purified by recrystallization from hexane-CH2Cl2

Sources & evidence

ORD record
ord-46ff9619c30c4a8f9109a39b3fb8119a
Source dataset
uspto-grants-2003_07
Patent number
US06596445B1

Reaction notes

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