Hydrogen Peroxide → HCID 58706319, compound

HRID 1990854Notes

Reaction equation

HRID 1990854 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:9]=[C:10]([O:14][CH2:15][CH3:16])[C:11]=1[S:12][CH3:13])[CH:7]=[O:8])[CH3:2].[OH:17]O.O>C(O)(=O)C>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:9]=[C:10]([O:14][CH2:15][CH3:16])[C:11]=1[S:12]([CH3:13])=[O:17])[CH:7]=[O:8])[CH3:2]

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 962WaterHCID 58706349HCID 58706349, compound

Product 1

HCID 58706319HCID 58706319, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 3,5-diethoxy-4-methylsulfanyl-benzaldehyde (0.28 g, 1.16 mmol, 1.0 equiv) in conc. acetic acid (5 mL) was added a solution of 35% hydrogen peroxide in water (0.13 mL, 0.15 g, 1.50 mmol, 1.3 equiv). After stirring the solution for 2 h at rt the reaction mixture was extracted with ethyl acetate (3×50 mL) and the combined organic phases dried over MgSO4. The organic solvent was removed by evaporation under reduced pressure and the crude material purified with column chromatography on silica eluting with ethyl acetate (1% methanol) providing 0.25 g (84%) of the title compound. 1H NMR (300 MHz, CDCl3): δ 1.50 (t, J=7.0 Hz, 6H), 3.11 (s, 3H), 4.15-4.26 (m, 4H), 7.07 (s, 2H), 9.93 (s, 1H). 13C NMR (75 MHz, CDCl3): δ 14.50, 37.62, 65.34, 106.10, 125.13, 139.95, 159.53, 191.07. MS (ISP): 257.1 [M+H]+.

Workup

  1. extractionwas extracted with ethyl acetate (3×50 mL)
  2. dry with materialthe combined organic phases dried over MgSO4
  3. customThe organic solvent was removed by evaporation under reduced pressure
  4. customthe crude material purified with column chromatography on silica eluting with ethyl acetate (1% methanol)

Sources & evidence

ORD record
ord-a86690d2353b45228b777016035d9391
Source dataset
uspto-grants-2010_01
Patent number
US07645753B2

Reaction notes

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