Hydrogen Peroxide → HCID 86732889, compound

HRID 1579587Notes

Reaction equation

HRID 1579587 reaction equation
[CH2:1]([S:4][C:5]1[C:6](=[O:13])[O:7][C:8]([CH3:12])=[CH:9][C:10]=1[OH:11])[CH:2]=[CH2:3].[OH:14]O>C(O)(=O)C>[CH2:1]([S:4]([C:5]1[C:6](=[O:13])[O:7][C:8]([CH3:12])=[CH:9][C:10]=1[OH:11])=[O:14])[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 784Hydrogen PeroxideHCID 54738346HCID 54738346, compound

Product 1

HCID 86732889HCID 86732889, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

3-Allylthio-4-hydroxy-6-methyl-2-pyrone (5.95 g., 0.0300 mol), 30% hydrogen peroxide (3.85 g., 0.0330 mol), and 40 ml. glacial acetic acid were combined and stirred over night at room temperature. The clear solution was poured into 250 ml. ice water. The aqueous mixture was extracted with clhoroform. The CHCl3 was dried (Na2SO4) and evaporated in vacuo. The recovered pink solid was recrystallized from cyclohexane-benzene to recover 5.0 g. (78 percent) of the desired compound. One additional recrystallization from cyclohexane-n-hexane gave the pure compound, m.p. 111°-112°C.

Workup

  1. additionThe clear solution was poured into 250 ml
  2. extractionThe aqueous mixture was extracted with clhoroform
  3. dry with materialThe CHCl3 was dried (Na2SO4)
  4. customevaporated in vacuo
  5. customThe recovered pink solid was recrystallized from cyclohexane-benzene
  6. customto recover 5.0 g
  7. customOne additional recrystallization from cyclohexane-n-hexane
  8. customgave the pure compound, m.p. 111°-112°C.

Sources & evidence

ORD record
ord-0b54da1c7c744bb6bab077bb6935b1b7
Source dataset
uspto-grants-1976_01
Patent number
US03931235

Reaction notes

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