Hydrogen Peroxide → 3-(o-Fluorobenzylsulfinyl)-4-hydroxy-6-methyl-2-pyrone

HRID 1579598Notes

Reaction equation

HRID 1579598 reaction equation
[F:1][C:2]1[CH:18]=[CH:17][CH:16]=[CH:15][C:3]=1[CH2:4][S:5][C:6]1[C:7](=[O:14])[O:8][C:9]([CH3:13])=[CH:10][C:11]=1[OH:12].[OH:19]O>C(O)(=O)C>[F:1][C:2]1[CH:18]=[CH:17][CH:16]=[CH:15][C:3]=1[CH2:4][S:5]([C:6]1[C:7](=[O:14])[O:8][C:9]([CH3:13])=[CH:10][C:11]=1[OH:12])=[O:19]

Participants

4

Reactant 2

HCID 784Hydrogen PeroxideHCID 54729787HCID 54729787, compound

Product 1

HCID 547327133-(o-Fluorobenzylsulfinyl)-4-hydroxy-6-methyl-2-pyrone

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

3-(o-Fluorobenzylthio)-4-hydroxy-6-methyl-2-pyrone (13.8 g., 0.0519 mole) and 30% hydrogen peroxide (5.9 g., 0.0519 mole) were mixed with glacial acetic acid (100 ml.) with stirring. After ten days the peroxide had been consumed, and the solution was diluted with water. The resulting mixture was extracted with methylene chloride. The extract was dried (MgSO4) and evaporated to dryness, leaving 13.3 g. (91 percent) of a colored solid. Recrystallization from a mixed hexane-benzene solution gave the pure product as a white solid, m.p. 115°-116°C.

Workup

  1. customAfter ten days the peroxide had been consumed
  2. additionthe solution was diluted with water
  3. extractionThe resulting mixture was extracted with methylene chloride
  4. dry with materialThe extract was dried (MgSO4)
  5. customevaporated to dryness
  6. customleaving 13.3 g
  7. customRecrystallization from a mixed hexane-benzene solution

Sources & evidence

ORD record
ord-a748d1e9672948ab9310341c9f105a2b
Source dataset
uspto-grants-1976_01
Patent number
US03931235

Reaction notes

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