Water → Benzene, 1-chloro-4-(4-(methylsulfonyl)phenoxy)-

HRID 2164626Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[OH-].[Na+].[CH3:11][S:12]([C:15]1[CH:20]=[CH:19][C:18](Cl)=[CH:17][CH:16]=1)(=[O:14])=[O:13].O>CS(C)=O>[CH3:11][S:12]([C:15]1[CH:20]=[CH:19][C:18]([O:8][C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)=[CH:17][CH:16]=1)(=[O:14])=[O:13]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 7.41 g (0.0576 mole) of 4-chlorophenol dissolved in 150 ml of DMSO was added 2.30 g (0.0576 mole) of 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 160° C. for 3 hrs and cooled. The mixture was poured into a solution of 400 ml of 2 Normal (N) aqueous NaOH and 300 ml of water. The crystalline product was collected by filtration, washed well with water, and dried, which gave 13.8 g (93.2% yield) of product, mp 109°-111° C. Recrystallization from ethanol afforded purified 4-(4-(methylsulfonyl)phenoxy)-1-chlorobenzene, mp 111°-112° C.

Workup

temperatureThe reaction mixture was heated at 160° C. for 3 hrs
temperaturecooled
filtrationThe crystalline product was collected by filtration
washwashed well with water
customdried

Sources & evidence

ORD record: ord-a95104c3aa694ddfa3fbdd6037acf2f4
Source dataset: uspto-grants-1985_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04505929

Reaction notes

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