Hydrogen Peroxide → HCID 20536114, compound

HRID 1447741Notes

Reaction equation

HRID 1447741 reaction equation
[F:1][C:2]([F:25])([F:24])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[S:9][C:10]1[CH:23]=[CH:22][C:13]([O:14][CH:15]([CH3:21])[C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:12][CH:11]=1.OO.S(=O)(O)[O-:29].[Na+]>S(=O)(=O)(O)O.C(O)(=O)C>[F:25][C:2]([F:24])([F:1])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[S:9]([C:10]1[CH:23]=[CH:22][C:13]([O:14][CH:15]([CH3:21])[C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:12][CH:11]=1)=[O:29]

Participants

6

Reactant 3

HCID 784Hydrogen PeroxideHCID 20382452HCID 20382452, compoundHCID 23665763Sodium Bisulfite

Product 1

HCID 20536114HCID 20536114, compound

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 176Acetic AcidSolvent2×

Procedure

To a stirred solution containing 7.4 g. (0.020 mole) of ethyl 2-[4-(2-trifluoromethylphenylthio)phenoxy]propionate and a catalytic amount of sulfuric acid (3 drops) in 50 ml of glacial acetic acid is added a solution containing 2.23 g. (0.021 mole) of 32% hydrogen peroxide in 10 ml. of glacial acetic acid over a period of several minutes at 25°. The resultant solution is stirred for 24 hours under ambient conditions, at which time the reaction is essentially complete. After the reaction mixture is treated with sodium bisulfite to destroy any excess peroxide the solvent is removed in vacuo at 40° and the residue taken-up in ether. The ethereal solution is washed with a 5% potassium carbonate solution until basic, water until neutral, a saturated sodium chloride solution, dried with magnesium sulfate, and concentrated in vacuo to give 6.85 g. of material. The last traces of solvent are removed by exposure to high vacuum (0.1 mm) at 70° to afford ethyl 2-[4-(2-trifluoromethylphenylsulfinyl)phenoxy]propionate.

Workup

  1. additionTo a stirred solution containing 7.4 g
  2. additioncontaining 2.23 g
  3. customto destroy any excess peroxide the solvent
  4. customis removed in vacuo at 40°
  5. washThe ethereal solution is washed with a 5% potassium carbonate solution until basic, water until neutral, a saturated sodium chloride solution
  6. dry with materialdried with magnesium sulfate
  7. concentrationconcentrated in vacuo
  8. customto give 6.85 g
  9. customThe last traces of solvent are removed by exposure to high vacuum (0.1 mm) at 70°

Sources & evidence

ORD record
ord-9323839a545f4247858cbee5816b5cf0
Source dataset
uspto-grants-1979_12
Patent number
US04178169

Reaction notes

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