Hydrogen Peroxide → HCID 21555255, compound

HRID 267605Notes

Reaction equation

HRID 267605 reaction equation
[CH2:1]([S:8][C:9]1[C:10](=[O:18])[CH2:11][C:12]([CH3:17])([CH3:16])[CH2:13][C:14]=1[OH:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH:19]O>C(O)(=O)C>[CH2:1]([S:8]([C:9]1[C:14](=[O:15])[CH2:13][C:12]([CH3:16])([CH3:17])[CH2:11][C:10]=1[OH:18])=[O:19])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 784Hydrogen PeroxideHCID 21555250HCID 21555250, compound

Product 1

HCID 21555255HCID 21555255, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 10.3 g. (0.0391 mole) of 2-benzylthio-3-hydroxy-5,5-dimethyl-2-cyclohexen-1-one and 4.43 g. (0.0391 mole) of 30 percent hydrogen peroxide in 50 ml. of glacial acetic acid was allowed to stand at room temperature for 22 hours and was then poured into ice water and the mixture extracted with methylene chloride. The extract was dried over anhydrous sodium sulfate, filtered and the solvent removed by evaporation in vacuo, leaving 9.2 g. of amber viscous oil. After some difficulty in inducing crystallization, seed crystals were obtained by an ether solution of a small portion of the oil in a Dry Ice methylene chloride bath. The seed crystals, thus obtained, were used to induce crystallization of the main portion of the oil from ether-hexane to give 7.8 g. of light-pink crystals, m.p. 82°-83°C. A second recrystallization from ether-hexane gave the pure substance as light pink crystals, m.p. 82.5°-83.5°C.

Workup

  1. extractionthe mixture extracted with methylene chloride
  2. dry with materialThe extract was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. customthe solvent removed by evaporation in vacuo
  5. customleaving 9.2 g
  6. customcrystallization
  7. customseed crystals were obtained by an ether solution of a small portion of the oil in a Dry Ice methylene chloride bath
  8. customThe seed crystals, thus obtained
  9. customcrystallization of the main portion of the oil from ether-hexane
  10. customto give 7.8 g
  11. customA second recrystallization from ether-hexane
  12. customgave the pure substance as light pink crystals, m.p. 82.5°-83.5°C.

Sources & evidence

ORD record
ord-4ea4a1fd9fea4fd9874a3b61e97cc93f
Source dataset
uspto-grants-1976_03
Patent number
US03943176

Reaction notes

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