Sodium Hydroxide → 1-(Methylsulfonyl)-4-(4-nitrophenoxy)benzene

HRID 336439Notes

Reaction equation

HRID 336439 reaction equation
[CH3:1][S:2][C:3]1[CH:18]=[CH:17][C:6]([O:7][C:8]2[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][CH:9]=2)=[CH:5][CH:4]=1.C1C=C(Cl)C=C(C(OO)=[O:27])C=1.[OH-:30].[Na+]>ClCCl>[CH3:1][S:2]([C:3]1[CH:18]=[CH:17][C:6]([O:7][C:8]2[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][CH:9]=2)=[CH:5][CH:4]=1)(=[O:27])=[O:30]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 70297m-Chloroperbenzoic acidHCID 13078526HCID 13078526, compound

Product 1

HCID 5148741-(Methylsulfonyl)-4-(4-nitrophenoxy)benzeneYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-(4-Methylsulfanylphenoxy)-4-nitrobenzene (86 g, 330 mmol) prepared in Step A was dissolved in dichloromethane (500 mL). mCPBA (3-chloroperbenzoic acid) (83 g, 330 mmol) was added thereto, and the mixture was stirred for 2 h at 0° C. to room temperature. After completion of the reaction, excess 6N aqueous sodium hydroxide solution was added. The reaction mixture was extracted with ethyl acetate and dichloromethane, washed with saturated sodium chloride solution, and dried over anhydrous magnesium sulfate to give the title compound (28 g, Yield 100%).

Workup

  1. additionwas added
  2. extractionThe reaction mixture was extracted with ethyl acetate and dichloromethane
  3. washwashed with saturated sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate

Sources & evidence

ORD record
ord-00a0a9e5df5644d0916e2589ab8f7023
Source dataset
uspto-grants-2014_11
Patent number
US08889691B2

Reaction notes

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