Toluene → 1-Chloro-3-(2-methoxyethoxy)-2-methyl-4-(methylsulfonyl)benzene
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH3:11])(=[O:10])=[O:9])=[C:4](Cl)[C:3]=1[CH3:13].C1(C)C=CC=CC=1.[OH-].[Na+].[CH3:23][O:24][CH2:25][CH2:26][OH:27]>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH3:11])(=[O:10])=[O:9])=[C:4]([O:27][CH2:26][CH2:25][O:24][CH3:23])[C:3]=1[CH3:13]Participants
5
Procedure
1,3-Dichloro-2-methyl-4-(methylsulfonyl)benzene (13.1 g) and toluene (40 mL) were mixed, and 2-methoxyethanol (4.49 g) and sodium hydroxide (4.55 g) were added, followed by heating and refluxing for 3 hours. After completion of the reaction, the mixture was cooled to room temperature, and the solvent was distilled off under reduced pressure. To the obtained residue, a mixed solvent of methanol (12 mL) and water (48 mL) was added, followed by stirring for a while. Then, the formed solid was collected by filtration, further washed with water and dried to obtain 1-chloro-3-(2-methoxyethoxy)-2-methyl-4-(methylsulfonyl)benzene (12.4 g) as slightly yellow solid.