Hydrogen Peroxide → HCID 54539508, compound

HRID 370319Notes

Reaction equation

HRID 370319 reaction equation
[CH3:1][C:2](=[CH:8][C:9]1[CH:14]=[CH:13][C:12](SC)=[CH:11][CH:10]=1)[C:3]([O:5][CH2:6][CH3:7])=[O:4].[OH:17][S:18]([OH:21])(=O)=O.OO.S([O-])([O-])=O.[Na+].[Na+].[CH3:30]O>O>[CH3:1][C:2](=[CH:8][C:9]1[CH:10]=[CH:11][C:12]([S:18]([CH3:30])(=[O:21])=[O:17])=[CH:13][CH:14]=1)[C:3]([O:5][CH2:6][CH3:7])=[O:4]

Participants

7

Reactant 5

HCID 784Hydrogen PeroxideHCID 887MethanolHCID 1118Sulfuric AcidHCID 24437Sodium SulfiteHCID 54416712HCID 54416712, compound

Product 1

HCID 54539508HCID 54539508, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of sulfide 6a (2.36 g, 10 mmol), Na2WO4 ·2 H2O (49.5 mg, 0.15 mmol), and H2SO4 (1 M, 68 μL) in methanol (10 mL) was added dropwise 30% H2O2 (2.6 mL) at room temperature under nitrogen maintaining the temperature at 38-45° C. The mixture was aged at ambient temperature for 3 h and cooled ~18° C. Sodium sulfite (20% aqueous solution, 2.6 mL) was added slowly with an external cooling to maintain the temperature below 20° C. After aged for 0.5 h the mixture was diluted with water (20 mL) and filtered. The solid was washed with water (2×10 mL) and dried in vacuo to give 2.55 g of 6b as a light yellow solid: IR (thin film) 1700 cm-1 ; 1H NMR (CDCl3, 300 MHz) δ 7.92 (2 H), 7.64 (1 H), 7.52 (2 H), 4.24 (2 H), 3.04 (3 H), 2.05 (3 H), and 1.30 (3 H); 13C NMR (CDCl3, 75.5 MHz) δ 167.88, 141.50, 139.76, 136.29, 131.87, 130.21, 127.45, 61.24, 44.45, 14.28, and 14.14.

Workup

  1. temperaturecooled ~18° C
  2. temperaturean external cooling
  3. temperatureto maintain the temperature below 20° C
  4. waitAfter aged for 0.5 h
  5. filtrationfiltered
  6. washThe solid was washed with water (2×10 mL)
  7. customdried in vacuo

Sources & evidence

ORD record
ord-6992b0968c7340f1ace22ca26b5668fd
Source dataset
uspto-grants-2000_10
Patent number
US06140515

Reaction notes

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