Hydrogen Peroxide → HCID 54736283, compound

HRID 1579591Notes

Reaction equation

HRID 1579591 reaction equation
[Cl:1][C:2]1[CH:18]=[CH:17][C:5]([CH2:6][S:7][C:8]2[C:9](=[O:16])[O:10][C:11]([CH3:15])=[CH:12][C:13]=2[OH:14])=[CH:4][CH:3]=1.[OH:19]O>C(O)(=O)C>[Cl:1][C:2]1[CH:18]=[CH:17][C:5]([CH2:6][S:7]([C:8]2[C:9](=[O:16])[O:10][C:11]([CH3:15])=[CH:12][C:13]=2[OH:14])=[O:19])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 784Hydrogen PeroxideHCID 54735213HCID 54735213, compound

Product 1

HCID 54736283HCID 54736283, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

3-p-Chlorobenzylthio-4-hydroxy-6-methyl-2-pyrone (11.3 g., 0.0400 mol), 30% hydrogen peroxide (5.14 g., 0.0440 mol) and 50 ml. glacial acetic acid were combined and stirred at room temperature for 4 hours. Then stored at room temperature over night. The reaction mixture, containing a crystalline solid, was added to 200 ml. of icewater. The precipitate was collected and dried. The solids were recrystallized from a mixture of cyclohexane-toluene to recover 8.6 g. (72 percent) of the desired compound, m.p. 150°-151°C. One additional recrystallization from cyclo-hexane-toluene gave the pure compound as white platelets, m.p. 151°-152°C.

Workup

  1. waitThen stored at room temperature over night
  2. additionThe reaction mixture, containing a crystalline solid
  3. additionwas added to 200 ml
  4. customThe precipitate was collected
  5. customdried
  6. customThe solids were recrystallized from a mixture of cyclohexane-toluene
  7. customto recover 8.6 g
  8. customOne additional recrystallization from cyclo-hexane-toluene
  9. customgave the pure compound as white platelets, m.p. 151°-152°C.

Sources & evidence

ORD record
ord-0723a51b1c7749be92fe3c73ba35d1e0
Source dataset
uspto-grants-1976_01
Patent number
US03931235

Reaction notes

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