Acetic Acid → HCID 54737320, compound

HRID 1579586Notes

Reaction equation

HRID 1579586 reaction equation
[CH2:1]([S:8][C:9]1[C:10](=[O:17])[O:11][C:12]([CH3:16])=[CH:13][C:14]=1[OH:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.OO.C(O)(=[O:22])C>C1(C)C=CC=CC=1.C(O)C>[CH2:1]([S:8]([C:9]1[C:10](=[O:17])[O:11][C:12]([CH3:16])=[CH:13][C:14]=1[OH:15])=[O:22])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 176Acetic Acid2×HCID 784Hydrogen PeroxideHCID 54729468HCID 54729468, compound

Product 1

HCID 54737320HCID 54737320, compoundYield 69%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 1140TolueneSolvent

Procedure

3-Benzylthio-4-hydroxy-6-methyl-2-pyrone (7.45 g., 0.0282 mol) and 30% hydrogen peroxide (3.7 g., 0.033 mol) were combined in 30 ml. glacial acetic acid and stirred at room temperature for 20 hours. The solution was then diluted with a mixture of toluene and ethanol (5:1) and warmed in vacuo to codistil the acetic acid. The recovered tan solid was recrystallized from toluene (DARCO) to give 5.4 g. (69 percent) of the desired product: m.p. 150°-153°C. One additional recrystallization from toluene gave the pure compound: m.p. 155°-156°C.

Workup

  1. temperaturewarmed in vacuo
  2. customThe recovered tan solid was recrystallized from toluene (DARCO)
  3. customto give 5.4 g

Sources & evidence

ORD record
ord-ec324c6e22984bc4ba83e2f021e57bd1
Source dataset
uspto-grants-1976_01
Patent number
US03931235

Reaction notes

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