Water → Benzene, 1,2-dichloro-4-(4-(methylsulfonyl)phenoxy)-

HRID 1702810Notes

Reaction equation

HRID 1702810 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)=[CH:18][CH:17]=1)(=[O:15])=[O:14].O>CS(C)=O>[CH3:12][S:13]([C:16]1[CH:21]=[CH:20][C:19]([O:9][C:4]2[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=2)=[CH:18][CH:17]=1)(=[O:15])=[O:14]

Participants

6

Reactant 4

HCID 962WaterHCID 72583,4-DichlorophenolHCID 73951-Chloro-4-(methylsulfonyl)benzeneHCID 14798Sodium Hydroxide

Product 1

HCID 514859Benzene, 1,2-dichloro-4-(4-(methylsulfonyl)phenoxy)-Yield 77.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 9.40 grams (g) (0.0576 mole) of 3,4-dichlorophenol dissolved in 150 milliliters (ml) of dimethyl sulfoxide (DMSO) was added 2.30 g (0.0576 mole) of sodium hydroxide (NaOH). The mixture was heated to 60° C. and 10.0 g (0.0524 mole) of 4-chlorophenyl methyl sulfone was added. The reaction mixture was heated at 165° C. for 2.5 hours (hrs) and cooled. The mixture was poured into water and the crystalline product collected by filtration, washed well with water and dried, which gave 12.8 g (77.1% yield) of product. Recrystallization from ethanol afforded purified 4-(4-(methylsulfonyl)phenoxy)-1,2-dichlorobenzene, melting at a melting point (mp) of 124.5°-125.5° C.

Workup

  1. temperatureThe reaction mixture was heated at 165° C. for 2.5 hours (hrs)
  2. temperaturecooled
  3. filtrationthe crystalline product collected by filtration
  4. washwashed well with water
  5. customdried

Sources & evidence

ORD record
ord-cc435efb3b404f92a84573e2cac72185
Source dataset
uspto-grants-1982_09
Patent number
US04349568

Reaction notes

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