Acetic Acid → 1-Methyl-2-(propane-1-sulfinyl)-4-[3-(trifluoromethyl)phenoxy]benzene

HRID 372461Notes

Reaction equation

HRID 372461 reaction equation
OO.[F:3][C:4]([F:24])([F:23])[C:5]1[CH:6]=[C:7]([O:11][C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[C:14]([S:19][CH2:20][CH2:21][CH3:22])[CH:13]=2)[CH:8]=[CH:9][CH:10]=1.C(O)(=[O:27])C>O>[F:24][C:4]([F:23])([F:3])[C:5]1[CH:6]=[C:7]([O:11][C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[C:14]([S:19]([CH2:20][CH2:21][CH3:22])=[O:27])[CH:13]=2)[CH:8]=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 784Hydrogen PeroxideHCID 203277371-Methyl-2-(propylsulfanyl)-4-[3-(trifluoromethyl)phenoxy]benzene

Product 1

HCID 203277391-Methyl-2-(propane-1-sulfinyl)-4-[3-(trifluoromethyl)phenoxy]benzeneYield 92.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Thirty-five percent hydrogen peroxide solution (1.6 g, 0.016 mole) was added at 8°-10° C to a mixture of 4-methyl-3-n-propylthiophenyl 3-trifluoromethylphenyl ether (3.8 g, 0.012 mole) and glacial acetic acid (30 ml). After 5 hr at room temperature, the reaction mixture was poured into water (100 ml) and extracted three times with benzene. The combined organic layers were washed with 5 % sodium carbonate solution, then water and dried over sodium sulfate. Evaporation of the solvent gave 3.8 g (92.5 %) of 4-methyl-3-n-propylsulfinylphenyl 3-trifluoromethylphenyl ether, colorless oil, nD25 1.5350. Anal. Found: C, 59.50; H, 5.11. Calcd. for C17H17F3O2S : C, 59.64; H, 5.01 %.

Workup

  1. extractionextracted three times with benzene
  2. washThe combined organic layers were washed with 5 % sodium carbonate solution
  3. dry with materialwater and dried over sodium sulfate
  4. customEvaporation of the solvent

Sources & evidence

ORD record
ord-1bb90181fa874e4ba35faf3008ac7e8d
Source dataset
uspto-grants-1978_05
Patent number
US04091109

Reaction notes

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