Hydrogen Peroxide → 3-(1-Adamantylsulfinyl)-4-hydroxy-6-methyl-2-pyrone

HRID 1579605Notes

Reaction equation

HRID 1579605 reaction equation
[C:1]12([S:11][C:12]3[C:13](=[O:20])[O:14][C:15]([CH3:19])=[CH:16][C:17]=3[OH:18])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[OH:21]O>C(O)(=O)C>[C:1]12([S:11]([C:12]3[C:13](=[O:20])[O:14][C:15]([CH3:19])=[CH:16][C:17]=3[OH:18])=[O:21])[CH2:8][CH:7]3[CH2:9][CH:3]([CH2:4][CH:5]([CH2:6]3)[CH2:10]1)[CH2:2]2

Participants

4

Reactant 2

HCID 784Hydrogen PeroxideHCID 547361873-(1-Adamantylthio)-4-hydroxy-6-methyl-2-pyrone

Product 1

HCID 547383153-(1-Adamantylsulfinyl)-4-hydroxy-6-methyl-2-pyrone

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 2.0 g. (0.0068 mole) of 3-(1-adamantylthio)-4-hydroxy-6-methyl-2-pyrone in 50 ml. of glacial acetic acid was added 0.78 g. (0.0070 mole) of 30% hydrogen peroxide and the solution allowed to stand at room temperature for 19 hours. The solution was then poured into ice water, and the resulting white solid precipitate was collected on a filter and recrystallized from ethanol to give the pure product 3-(1-adamantylsulfinyl)-4-hydroxy-6-methyl- 2-pyrone as 1.67 g. (80 percent) of colorless needles, m.p. 174.5°C.

Workup

  1. customthe resulting white solid precipitate was collected on
  2. filtrationa filter
  3. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-36a7a80479744dc29ec34e35252f9b4b
Source dataset
uspto-grants-1976_01
Patent number
US03931235

Reaction notes

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