Water → HCID 13078530, compound

HRID 2164636Notes

Reaction equation

HRID 2164636 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[CH:6][C:7]=1[Cl:8].[OH-].[Na+].[CH3:12][S:13]([C:16]1[CH:21]=[CH:20][C:19](Cl)=[C:18]([Cl:23])[CH:17]=1)(=[O:15])=[O:14].O>CS(C)=O>[Cl:23][C:18]1[CH:17]=[C:16]([S:13]([CH3:12])(=[O:15])=[O:14])[CH:21]=[CH:20][C:19]=1[O:9][C:4]1[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 72583,4-DichlorophenolHCID 14798Sodium HydroxideHCID 161963Benzene, 1,2-dichloro-4-(methylsulfonyl)-

Product 1

HCID 13078530HCID 13078530, compoundYield 82.4%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 9.09 g (0.0558 mole) of 3,4-dichlorophenol dissolved in 150 ml of DMSO was added 2.23 g (0.0558 mole) of NaOH. The mixture was heated to 60° C. and 11.3 g (0.0502 mole) of 3,4-dichlorophenyl methyl sulfone was added and the mixture heated at 150° C. for 3.75 hrs. The mixture was cooled and poured into water. The crystalline product was collected by filtration, washed with water and dried, which gave 14.5 g (82.4% yield) of product. Recrystallization from ethanol afforded purified 4-(2-chloro-4-(methylsulfonyl)phenoxy)-1,2-dichlorobenzene, mp 102°-104° C.

Workup

  1. temperaturethe mixture heated at 150° C. for 3.75 hrs
  2. temperatureThe mixture was cooled
  3. filtrationThe crystalline product was collected by filtration
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-8302003fc81d4384ba016f79de96227c
Source dataset
uspto-grants-1985_03
Patent number
US04505929

Reaction notes

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