Thioanisole → 1-(4-(methylthio)phenyl)-2-phenylethanone
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]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
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)