1-Chloro-4-(methylsulfonyl)benzene → Benzene, 1-methoxy-4-(4-(methylsulfonyl)phenoxy)-

HRID 1702823Notes

Reaction equation

HRID 1702823 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8](Cl)=[CH:7][CH:6]=1)(=[O:4])=[O:3].[CH3:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=1.C([O-])([O-])=O.[K+].[K+].[OH-].[Na+]>S1(CCCC1)(=O)=O>[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([O:20][C:17]2[CH:18]=[CH:19][C:14]([O:13][CH3:12])=[CH:15][CH:16]=2)=[CH:7][CH:6]=1)(=[O:4])=[O:3]

Participants

6

Reactant 4

HCID 73951-Chloro-4-(methylsulfonyl)benzeneHCID 90154-MethoxyphenolHCID 11430Potassium CarbonateHCID 14798Sodium Hydroxide

Product 1

HCID 514881Benzene, 1-methoxy-4-(4-(methylsulfonyl)phenoxy)-Yield 85.4%

Reagents, catalysts & solvents 1

HCID 31347SulfolaneSolvent

Conditions

Temperature
160 °C

Procedure

To a solution of 38.1 g of 4-chlorophenyl methyl sulfone and 37.2 g of 4-methoxyphenol dissolved in 150 ml of sulfolane was added 41.5 g of K2CO3. The mixture was heated at 160° C. for 7 hrs and then at 170° C. for 14.5 hrs and cooled. The mixture was poured into aqueous NaOH and the crystalline product collected by filtration, washed well with water and dried, which gave 47.5 g (85.3% yield) of product. Recrystallization from ethanol gave purified 4-(4-(methylsulfonyl)phenoxy)-1-methoxybenzene, mp 151.5°-153° C.

Workup

  1. temperaturecooled
  2. filtrationthe crystalline product collected by filtration
  3. washwashed well with water
  4. customdried

Sources & evidence

ORD record
ord-9df9b0475ce14286b98ac05573df511d
Source dataset
uspto-grants-1982_09
Patent number
US04349568

Reaction notes

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