1-Chloro-4-(methylsulfonyl)benzene → 1-(4-(Methylsulfonyl)phenoxy)-4-(phenylmethyl)benzene

HRID 2164641Notes

Reaction equation

HRID 2164641 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].[CH2:12]([C:19]1[CH:24]=[CH:23][C:22]([OH:25])=[CH:21][CH:20]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C([O-])([O-])=O.[K+].[K+]>CS(C)=O>[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([O:25][C:22]2[CH:21]=[CH:20][C:19]([CH2:12][C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=3)=[CH:24][CH:23]=2)=[CH:7][CH:6]=1)(=[O:4])=[O:3]

Participants

5

Reactant 3

HCID 73951-Chloro-4-(methylsulfonyl)benzeneHCID 75634-BenzylphenolHCID 11430Potassium Carbonate

Product 1

HCID 130785181-(4-(Methylsulfonyl)phenoxy)-4-(phenylmethyl)benzeneYield 94.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A slurry of 5.72 g of 4-chlorophenyl methyl sulfone, 6.08 g of 4-benzylphenol and 4.56 g of K2CO3 in 150 ml of DMSO was heated at 160° C. for 8.5 hrs. The product (9.55 g, 94.1% yield) was recovered from the reaction mixture essentially as described in Example 18. Recrystallization from 2-propanol and then from aqueous acetic acid afforded purified 1-(4-(methylsulfonyl)phenoxy)-4-(phenylmethyl)benzene, mp 109°-110° C.

Sources & evidence

ORD record
ord-56714b215ca14aeda0b9c005b70b60df
Source dataset
uspto-grants-1985_03
Patent number
US04505929

Reaction notes

Loading…