Anisole → HCID 53953369, compound
Reaction equation
[Cl:1][C:2]1[C:10]([CH3:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4](Cl)=[O:5].[C:12]1([O:18][CH3:19])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>C(Cl)Cl>[CH3:19][O:18][C:12]1[CH:17]=[CH:16][C:15]([C:4]([C:3]2[C:2]([Cl:1])=[C:10]([CH3:11])[CH:9]=[CH:8][CH:7]=2)=[O:5])=[CH:14][CH:13]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
A solution of 2-chloro-3-methylbenzoyl chloride (18.05 mmol), [prepared as described above] in dry CH2Cl2 (60 ml) was cooled to 0° C. and AICl3 (2.41 g, 1 eq.) was added. After ten minutes, anisole (1.96 ml, 1 eq.) was added. The resulting orange colored reaction mixture was allowed to warm to room temperature, stirred for 3 h and then poured on ice. The product was extracted into ether, washed with brine, and dried over MgSO4 . The solvent was evaporated in vacuo to give 3-(4-methoxybenzoyl)-2-chlorotoluene (4.55 g, 97% yield) as a solid, mp 64.7°-65.8° C.