Toluene → 1-Chloro-3-(2-methoxyethoxy)-2-methyl-4-(methylsulfonyl)benzene

HRID 1257985Notes

Reaction equation

HRID 1257985 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

Reactant 4

HCID 1140TolueneHCID 80192-MethoxyethanolHCID 14798Sodium HydroxideHCID 672491791,3-Dichloro-2-methyl-4-(methylsulfonyl)benzene

Product 1

HCID 668856991-Chloro-3-(2-methoxyethoxy)-2-methyl-4-(methylsulfonyl)benzeneYield 81.2%

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.

Workup

  1. temperatureby heating
  2. temperaturerefluxing for 3 hours
  3. customAfter completion of the reaction
  4. distillationthe solvent was distilled off under reduced pressure
  5. additionTo the obtained residue, a mixed solvent of methanol (12 mL) and water (48 mL) was added
  6. filtrationThen, the formed solid was collected by filtration
  7. washfurther washed with water
  8. customdried

Sources & evidence

ORD record
ord-a2cd616ffb7741e5906d1d36092e2778
Source dataset
uspto-grants-2013_06
Patent number
US08466089B2

Reaction notes

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