Acetic Acid → HCID 54734732, compound

HRID 1579588Notes

Reaction equation

HRID 1579588 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][CH2:12][CH:13]([CH3:15])[CH3:14].OO.C(O)(=[O:20])C>C1(C)C=CC=CC=1.C(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][CH2:12][CH:13]([CH3:15])[CH3:14])=[O:20]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 784Hydrogen PeroxideHCID 54735605HCID 54735605, compound

Product 1

HCID 54734732HCID 54734732, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 1140TolueneSolvent

Procedure

4-Hydroxy-3-isopentylthio-6-methyl-2-pyrone (4.5 g., 0.020 mol), 30% hydrogen peroxide (2.44 g., 0.0220 mol), and 35 ml. glacial acetic acid were combined and stirred over night at room temperature. The clear solution was diluted with a mixture of toluene and ethanol and the acetic acid was removed by codistillation in vacuo. A yellow liquid was recovered which solidified upon cooling. The compound was recrystallized from n-hexane to recover 2.5 g. (51 percent) of shiny yellow platelets. One additional recrystallization from n-hexane gave the pure compound as tiny white crystalline needles: m.p. 80°-81°C.

Workup

  1. customthe acetic acid was removed by codistillation in vacuo
  2. customA yellow liquid was recovered which
  3. temperatureupon cooling
  4. customThe compound was recrystallized from n-hexane
  5. customto recover 2.5 g
  6. customOne additional recrystallization from n-hexane

Sources & evidence

ORD record
ord-c6d2d21ff1f047ee836600931f2e3679
Source dataset
uspto-grants-1976_01
Patent number
US03931235

Reaction notes

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