2-[4-(Methylthio)phenoxy]ethanol → Ethanol, 2-[4-(methylsulfonyl)phenoxy]-

HRID 330410Notes

Reaction equation

HRID 330410 reaction equation
CS[C:3]1[CH:12]=[CH:11][C:6]([O:7][CH2:8][CH2:9][OH:10])=[CH:5][CH:4]=1.Cl[C:14]1C(C2C=CC=CC=2)=C(C=CC=1)C(O)=O.[S:29](=[O:32])(O)[O-:30].[Na+]>C(Cl)Cl>[CH3:14][S:29]([C:3]1[CH:12]=[CH:11][C:6]([O:7][CH2:8][CH2:9][OH:10])=[CH:5][CH:4]=1)(=[O:32])=[O:30]

Participants

5

Reactant 3

HCID 148552542-[4-(Methylthio)phenoxy]ethanolHCID 23665763Sodium BisulfiteHCID 46314701m-Chlorophenylbenzoic acid

Product 1

HCID 14855255Ethanol, 2-[4-(methylsulfonyl)phenoxy]-

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 14.1 g (0.77 mole) of 2-[4-(methylthio)phenoxy]ethanol (from Preparation 35) and 31.2 g (0.18 mole) of m-chlorophenylbenzoic acid in 800 ml of methylene chloride was stirred at room temperature overnight. A saturated, aqueous solution (300 ml) of sodium bisulfite was added, and the mixture was stirred at room temperature for 0.5 hr. The phases were separated, the mthylene chloride solution was dried over magnesium sulfate, and the volume reduced to approximately 100 ml in vacuo. n-Hexane was added until the solution became cloudy, and 9.40 g (56.8%) of the product precipitated as a white, crystalline solid, m.p. 96°-98° C.

Workup

  1. customThe phases were separated
  2. dry with materialthe mthylene chloride solution was dried over magnesium sulfate
  3. additionn-Hexane was added until the solution
  4. customprecipitated as a white, crystalline solid, m.p. 96°-98° C.

Sources & evidence

ORD record
ord-ff8ab009a487420ea71eb7997bbd09c4
Source dataset
uspto-grants-1990_01
Patent number
US04895840

Reaction notes

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