Hydrogen Peroxide → 4-Hydroxy-6-methyl-3-propargylsulfinyl-2-pyrone

HRID 1579592Notes

Reaction equation

HRID 1579592 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([CH3:8])[O:5][C:4](=[O:9])[C:3]=1[S:10][CH2:11][C:12]#[CH:13].[OH:14]O>C(O)(=O)C>[OH:1][C:2]1[CH:7]=[C:6]([CH3:8])[O:5][C:4](=[O:9])[C:3]=1[S:10]([CH2:11][C:12]#[CH:13])=[O:14]

Participants

4

Reactant 2

HCID 784Hydrogen PeroxideHCID 547276744-Hydroxy-6-methyl-3-propargylthio-2-pyrone

Product 1

HCID 867328904-Hydroxy-6-methyl-3-propargylsulfinyl-2-pyrone

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent3×

Procedure

To a suspension of 23.1 g. (0.124 mole) of 4-hydroxy-6-methyl-3-propargylthio-2-pyrone in 200 ml. of glacial acetic acid was added 14.1 g. (0.124 mole) of 30% hydrogen peroxide in 50 ml. of glacial acetic acid dropwise over a period of 20 minutes. The reaction mixture was stirred at room temperature for approximately 60 hours and then poured into 400 ml. of ice water. When no precipitate appeared, the solution was extracted with four 100 ml. portions of chloroform, and the extract was dried over anhydrous sodium sulfate. The chloroform was removed by evaporation in vacuo, leaving a solid residue and some acetic acid. The latter was removed by desiccation over sodium hydroxide at 0.2 mm. Hg. for four hours. The crude product was then recrystallized from ethanol, giving 17.7 g. (67 percent) of pale yellow crystals, m.p. 131°-134°C. A second recrystallization from ethanol gave the pure 4-hydroxy-6-methyl-3-propargylsulfinyl-2-pyrone as pale yellow needles, m.p. 133.5°-134.5°C.

Workup

  1. additionTo a suspension of 23.1 g
  2. additionpoured into 400 ml
  3. extractionthe solution was extracted with four 100 ml
  4. dry with materialportions of chloroform, and the extract was dried over anhydrous sodium sulfate
  5. customThe chloroform was removed by evaporation in vacuo
  6. customleaving a solid residue
  7. customThe latter was removed by desiccation over sodium hydroxide at 0.2 mm. Hg
  8. waitfor four hours
  9. customThe crude product was then recrystallized from ethanol
  10. customgiving 17.7 g
  11. customA second recrystallization from ethanol

Sources & evidence

ORD record
ord-4c2c7196bbed4925a98dcce7f4f8db6c
Source dataset
uspto-grants-1976_01
Patent number
US03931235

Reaction notes

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